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D-Cycloserine and O-Carbamyl-D-serine

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Antibiotics

Abstract

Alanine is a major component of the peptidoglycan (mucopeptide) and teichoic acid moieties of bacterial cell walls (Salton, 1964). Part of the alanine in the wall is present as the d-isomer (39–50% in Streptococcus faecalis (Ikawa and Snell, 1960; Toennies and Shockman, 1959) and 67% in Staphylococcus aureus (Strominger et al, 1959). Salton (1961) has proposed that the occurrence of d-amino acids in the wall renders the bacterium resistant to proteolytic enzymes. Thus, it may be argued that the introduction of d-amino acids, e.g. d-alanine and d-glutamic acid, into the bacterial wall is a protective mechanism that the bacterium possesses against its environment.

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References

  • Aliot., M. R.: In vitro and in vivo action of cycloserine on L-alanine-alpha-ketoglutaric transaminases in rat liver. Biochim. Appl. 9., 238 (1962).

    CAS  Google Scholar 

  • Anderso., J. S., M. Matsuhash., M. A. Haski., and J. L. Strominge.: Lipidphosphodisaccharide-pentapeptide: A presumed membrane transport intermediate in the biosynthesis of bacterial cell walls. Proc. Natl. Acad. Sci. U.S. 5., 881 (1965).

    CAS  Google Scholar 

  • Aok., T.: The mode of action of cycloserine. II. The influence on glutamic-aspartic transamination. Kekkaku 3., 544 (1957)

    PubMed  CAS  Google Scholar 

  • Aok., T.: The mode of action of cycloserine. II. The influence on glutamic-aspartic transamination. Chem. Abstr. 5., 7427 (1958).

    Google Scholar 

  • Azark., R. M., A. E. Braunstei., T. S. Paskhin., and T. S. Syu.: The Effect of the optical isomers of cycloserine on the activity of certain transaminases. Biokhimiya 2., 954 (1960)

    CAS  Google Scholar 

  • Azark., R. M., A. E. Braunstei., T. S. Paskhin., and T. S. Syu.: The Effect of the optical isomers of cycloserine on the activity of certain transaminases. Biochemistry (U.S.S.R.) 2., 741 (1961).

    Google Scholar 

  • Barbier., P., A. DI Marc., I. Fuoco, and A. Ruscon.: Investigations on the mode of action of cycloserine upon protein synthesis in Escheyichia col Biochem. Pharmacol., 101 (1960).

    PubMed  CAS  Google Scholar 

  • Bonavit., V.: Purification and properties of glutamic-oxaloacetic transaminase from human brain. J. Neurochem., 275 (1959).

    PubMed  CAS  Google Scholar 

  • Bond., A., J. Kornblu., and C. Fort.: Inhibition of antibacterial activity of cycloserine by alpha-alanine. Proc. Soc. Exptl. Biol. Med. 9., 270 (1957).

    CAS  Google Scholar 

  • Botter., A., G. Pern., G. C. Colomb., and F. Leid.: Experimental and clinical studies on cycloserine resistance. Giorn. ital. tuberc. 1., 10 (1958).

    CAS  Google Scholar 

  • Braunstei., A. E.: Studies on the properties, mode of action, and selective inhibition of transaminase, In P. A. E. Desnuell. (Editor), Proceedings of the Fifth Internat. Congr. of Biochemistry, Moscow, 1962, vol. IV, p. 280. NewYork: Pergamon Press 1963.

    Google Scholar 

  • Braunstei., A. E., R. M. Azark., and T. A. Syu.: Kinetics of inhibition of transaminases by cycloserine. Biokhimiya 2., 882 (1961)

    Google Scholar 

  • Braunstei., A. E., R. M. Azark., and T. A. Syu.: Kinetics of inhibition of transaminases by cycloserine. Biochemistry (U.S.S.R.) 2., 760 (1962).

    Google Scholar 

  • Brettschneide., H., u. W. Vette.: Synthese des DL-4-Amino-3-isoxazOlidofs sowie seiner D-Form, des natürlichen Cycloserins. Monatsh. Chem. 9., 799 (1959).

    Google Scholar 

  • Brettschneide., H., W. Vette. u. E. Semenit.: Synthese und antibakterielle Eigenschaften des D,L-N,N-Dimethylcycloserins. Monatsh. Chem. 8., 627 (1958).

    Google Scholar 

  • Brege., M. A.: The biological activity of cycloserine and some of its analogues and homologues. Antibiotiki, 26 (1961).

    PubMed  CAS  Google Scholar 

  • Buog., A., A. DI Marc., M. Ghion., A. Migliacc., and A. Sanfilipp.: Antagonism of D- and L-alanine of the enantiomorphic forms of cycloserine. Giorn. microbiol., 131 (1958);

    CAS  Google Scholar 

  • Buog., A., A. DI Marc., M. Ghion., A. Migliacc., and A. Sanfilipp.: Antagonism of D- and L-alanine of the enantiomorphic forms of cycloserine. Chem. Abstr. 5., 17538 (1960).

    Google Scholar 

  • Chamber., P., J. Bin., J. Lync., F. C. Neuhau., and R. W. Brockma.: Effects of cycloserine and related compounds on cell wall synthesis in sensitive and resistant Escheyichia col Bacteriol. Proc. 119 (1963).

    Google Scholar 

  • Chatterje., A. N., and J. T. Par.: Biosynthesis of cell wall mucopeptide by a particulate fraction from Staphylococcus auveu Proc. Natl. Acad. Sci. U.S. 5., 9 (1964).

    CAS  Google Scholar 

  • Cia., J., and F. E. Hah.: Mechanisms of action of antibiotics. II. Studies on the modes of action of cycloserine and its L-stereoisomer. Antibiotics & Chemotherapy., 47 (1959).

    CAS  Google Scholar 

  • Cohe., A. C., and I. C. Dros.: High-dosage cycloserine in treatment failures. Transactions of the 19th conference on the chemotherapy of tuberculosis. Veterans Administration-Armed Forces, Washington, D. C., 173 (1960).

    Google Scholar 

  • Com., D. G.: The enzymatic addition of D-alanyl-D-alanine to a uridine nucleotide-peptide. J. Biol. Chem. 23., 1601 (1962).

    PubMed  CAS  Google Scholar 

  • Cuckle., A. C., B. M. Fros., L. Mcclellan., and M. Solotorovsk.: The antimicrobial evaluation of oxamycin (D-4-amino-3-isoxazolidone), a new broad-spectrum antibiotic. Antibiotics & Chemotherapy., 191 (1955).

    CAS  Google Scholar 

  • Cumming., M. M., R. A. Patnod., and P. C. Hudgin.: Effects of cycloserine on Mycobacterium tuberculosis in vitr Antibiotics & Chemotherapy., 198 (1955).

    CAS  Google Scholar 

  • Cumming., M. M.: Cycloserine: Resistance data. Transactions of the 15th conference on the chemotherapy of tuberculosis. Veterans Administration-Armed Forces, Washington, D. C., 377 (1956).

    Google Scholar 

  • Curtis., R., L. J. Charamell., C. M. Ber., and P. E. Harri.: Kinetic and genetic analyses of D-cycloserine inhibition and resistance in Escherichia col J. Bacteriol. 9., 1238 (1965).

    PubMed  CAS  Google Scholar 

  • Dan., O. T., and C. E. Carte.: Cycloserine inhibition of gamma-aminobutyric-alphaketoglutaric transaminase. Biochem. Pharmacology 1., 677 (1964).

    CAS  Google Scholar 

  • Davi., B. D., and M. K. Maa.: Analysis of the biochemical mechanism of drug resistance in certain bacterial mutants. Proc. Natl. Acad. Sci. U.S. 3., 775 (1952).

    CAS  Google Scholar 

  • Demere., M.: Origin of bacterial resistance to antibiotics. J. Bacteriol. 5., 63 (1948).

    PubMed  CAS  Google Scholar 

  • Dengle., H. J.: Zur Hemmung der L-Glutaminsäure-und L-Dopadecarboxylase durch D-Cycloserin und andere Isoxazolidone. Naunyn-Schmiedeberg’s Arch. Exptl. Pathol. u. Pharmakol 24., 366 (1962).

    CAS  Google Scholar 

  • Epstei., I. G., K. G. S. Nai., and L. J. Boy.: Cycloserine in the treatment of human pulmonary tuberculosis. Transactions of the 14th conference on the chemotherapy of tuberculosis. Veterans Administration-Armed Forces, Washington, D. C., 326 (1955).

    Google Scholar 

  • Fet., T., and K. Kazi.: In vitr. action of cycloserine on Mycobacterium tuberculosi Bacteriol. Proc. 85 (1962).

    Google Scholar 

  • Folker., K.: 4-Pyridoxylamino-3-isoxazolidone compounds. U.S. Patent., 776, 296 (January 1, 1957 ).

    Google Scholar 

  • Freckin., M. G., and P. D. Hoepric.: Effect of cycloserines on D-amino acid oxidase. Arch. Biochem. Biophys. 11., 108 (1966).

    PubMed  CAS  Google Scholar 

  • Frees., E., and J. Oosterwy.: The induction of alanine dehydrogenase. Biochemistry., 1212 (1963).

    PubMed  CAS  Google Scholar 

  • Grosse., J., and G. Canett.: Incidence of resistance to secondary antimicrobials in wild strains of M. tuberculosi. (Pa., ethionamide, cycloserine, viomycin, and kanamycin). Ann. Inst. Pasteur 10., 163 (1962).

    CAS  Google Scholar 

  • Grul., M. M., and E. A. Grul.: Action of cycloserine on a species of Erwini. with reference to cell division. Can. J. Microbiol. 1., 453 (1965).

    PubMed  CAS  Google Scholar 

  • Grul., E. A., and M. M. Grul.: Cell division in a species of Erwini Vi Amino sugar content of dividing and nondividing cells. Biochem. Biophys. Research Commun. 1., 341 (1964).

    CAS  Google Scholar 

  • Hageman., G., L. Penass. et J. Teillo.: Sur un derive de la serine, la O-carbamyl- D-serine produit par un streptomyces. Biochim. et Biophys. Acta 1., 240 (1955).

    CAS  Google Scholar 

  • Hah., F. E., and J. Cia.: Penicillin-induced lysis of Escherichia col Science 12., 119 (1957).

    PubMed  CAS  Google Scholar 

  • Hancoc., R., and P. C. Fit.-Jame.: Some differences in the action of penicillin, bacitracin, and vancomycin on Bacillus megateriu J. Bacteriol. 8., 1044 (1964).

    PubMed  CAS  Google Scholar 

  • Harne., R. L., P. H. Hid., and E. K. LA Ba.: Cycloserine. I. A preliminary report. Antibiotics & Chemotherapy., 204 (1955).

    CAS  Google Scholar 

  • Harri., D. A., M. Ruge., M. A. Reaga., F. J. Wol., R. L. Pec., H. Wallic., and H. B. Woodruf.: Discovery, development, and antimicrobial properties of D-4-amino-3-isoxazolidone (oxamycin), a new antibiotic produced by Streptomyces garyphalu. n. sp. Antibiotics & Chemotherapy., 183 (1955).

    CAS  Google Scholar 

  • Harri., D. A., F. J. Wol., and R. L. Pec.: Crystalline alkaline earth metal salts of 4-amino-3-isoxazolidone. U.S. Patent 2, 832, 788 (April 29, 1958 ).

    Google Scholar 

  • Hayash., K., C. G. Skinne., and W. Shiv.: Synthesis and biological properties of 4-amino-5-isopropyl-3-isoxazolidone, a substituted cycloserine. J. Org. Chem. 2., 1167 (1961).

    CAS  Google Scholar 

  • Hid., P. H., E. B. Hodg., V. V. Youn., R. L. Harne., G. A. Brewe., W. F. Phillip., W. F. Rung., H. E. Stavele., A. Pohlan., H. Boa., and H. R. Sulliva.: Structures and reactions of cycloserine. J. Am. Chem. Soc. 7., 2345 (1955).

    CAS  Google Scholar 

  • Hodg., E. B.: Substituted cycloserines. U.S. Patent 2,971,004 (February 7, 1961 ).

    Google Scholar 

  • Hodg., E. B.: N-(p-Chlorobenzyl)-cycloserine. U.S. Patent 2,967,866 (January 10, 1961 ).

    Google Scholar 

  • Hoepric., P. D.: Alanine: Cycloserine antagonism. Ii Quantitative aspects and relations to heating of culture media. J. Lab. Clin. Med. 6., 657 (1963).

    PubMed  CAS  Google Scholar 

  • Hoepric., P. D.: Alanine: Cycloserine antagonism. VI. Demonstration of D-alanine in the serum of guinea pigs and mice. J. Biol. Chem. 24., 1654 (1965).

    PubMed  CAS  Google Scholar 

  • Holl., F. W., Cranfor., and C. H. Stamme.: Synthesis of 4-amino-3-isoxazolidone and its derivatives. U.S. Patent 2, 772, 281 (November 27, 1956 ).

    Google Scholar 

  • How., W. B., G. L. Melso., C. H. Meredit., J. R. Morriso., M. H. Plat., and J. L. Strominge.: Stepwise development of resistance to D-cycloserine in Staphylococcus aureu J. Pharmacol. Exptl. Therap. 14., 282 (1964).

    CAS  Google Scholar 

  • Ikaw., M., and E. E. Snel.: Cell wall composition of lactic acid bacteria. J. Biol. Chem. 23., 1376 (1960).

    PubMed  CAS  Google Scholar 

  • Ishi., K., and M. G. Seva.: Inhibition by cycloserine of the synthesis of 5-amino-4-imidazolecarboxamide by Escherichia col Antibiotics & Chemotherapy., 500 (1956).

    CAS  Google Scholar 

  • It., E., and M. Sait.: Time course of accumulation of UDP-N-acetylamino sugar derivatives in Staphylococcus aureu Biochim. et Biophys. Acta 7., 237 (1963).

    CAS  Google Scholar 

  • IT., E., and J. L. Strominge.: Enzymatic synthesis of the peptide in bacterial uridine nucleotides. I. Enzymatic addition of L-alanine, D-glutamic acid, and L-lysine. J. Biol. Chem. 23., 2689 (1962a).

    CAS  Google Scholar 

  • It., E., and J. L. Strominge.: Enzymatic synthesis of the peptide in bacterial uridine nucleotides. II. Enzymatic synthesis and addition of D-alanyl-D-alanine. J. Biol. Chem. 23., 2696 (1962b).

    CAS  Google Scholar 

  • It., F., T. AoKI, M. Yamamot., M. Yuas., H. Mizobat., and K. Ton.: The mode of action of cycloserine (CS). Med. J. Osaka Univ., 23(1958).

    Google Scholar 

  • Karpeiski., M. YA., R. M. Khomuto., E. S. Severi., and Yu. N. Breuso.: The investigation of the interaction of cycloserine and related compounds with aspartate-glutamate transaminase. In: E. E. Snel., P. M. Fasell., A. E. Braunstei., and A. Ross.-Fanell. (editors), Chemical and Biological Aspects of Pyridoxal Catalysis. I.U.B. Symposium Series, vol. 30, p. 323. NewYork: Pergamon Press 1963a.

    Google Scholar 

  • Karpeiski., M. YA., Yu. N. Breuso., R. M. Khomuto., E. S. Severi., and O. L. Polyanovski.: The mechanism of reaction of cycloserine and related compounds with aspartate-glutamate transaminase. Biokhimiya 2., 345 (1963 b)

    CAS  Google Scholar 

  • Karpeiski., M. YA., Yu. N. Breuso., R. M. Khomuto., E. S. Severi., and O. L. Polyanovski.: The mechanism of reaction of cycloserine and related compounds with aspartate-glutamate transaminase. Biochemistry (U.S.S.R.) 2., 280 (1964).

    Google Scholar 

  • Karpeiski., M. YA., and YU. N. Breuso.: On the structure of the enzyme-inhibitor complex of aspartate-transaminase with L-cycloserine. Biokhimiya 3., 153 (1965).

    CAS  Google Scholar 

  • Khomuto., R. M., M. YA. Karpeiski., E. S. Severi., E. I. Budovski., and N. K. Kochetko.: Cycloserine and related compounds. VI. Synthesis of analogs of cycloserine with a substitued amino group. J. gen. Chem. (U.S.S.R.) 2., 636 (1959).

    Google Scholar 

  • Khomuto., R. M., M. YA. Karpeiski., C. C.I-Pi., and N. K. Kochetko.: Cycloserine and related compounds. XL. 4-Hydroxy-3-isoxazolidinone and some of its derivatives. Zhur. Obshchei Khim. 3., 3057 (1960)

    CAS  Google Scholar 

  • Khomuto., R. M., M. YA. Karpeiski., C. C.I-Pi., and N. K. Kochetko.: Cycloserine and related compounds. XL. 4-Hydroxy-3-isoxazolidinone and some of its derivatives. J. Gen. Chem. (U.S.S.R.) 3., 3030 (1961).

    Google Scholar 

  • Khomuto., R. M., M. YA. Karpeiski., and E. S. Severi.: The relationship between biological activity and chemical properties. Biokhimiya 2., 772 (1961)

    CAS  Google Scholar 

  • Khomuto., R. M., M. YA. Karpeiski., and E. S. Severi.: The relationship between biological activity and chemical properties. Biochemistry (U. S. S. R.) 2., 667 (1962).

    Google Scholar 

  • Khomuto., R. M., M. YA. Karpeiski., M. A. Brege., and E. S. Severi.: On some cycloserine derivatives possessing antitubercular activity. Voprosy Med. Khim., 389 (1962).

    CAS  Google Scholar 

  • Khomuto., R. M., M. YA. Karpeiski., and E. S. Severi.: The predetermined synthesis of inhibitors for pyridoxalic enzymes. In: E. E. Snel., P. M. Fasell., A. E. Braunstei., and A. Ross.-Fanell. (editors), Chemical and Biological Aspects of Pyridoxal Catalysis. I. U. B. Symposium Series, vol. 30, p. 323. New York: Pergamon Press 1963.

    Google Scholar 

  • Kihar., H., M. Ikaw., and E. E. Snel.: Peptides and bacterial growth. X. Relation of uptake and hydrolysis to utilization of D-alanine peptides for growth of Streptococcus faecali J. Biol. Chem. 23., 172 (1961).

    CAS  Google Scholar 

  • Kochetko., N. K., R. M. Khomuto., and M. YA. Karpeiski.: New synthesis of cycloserine. Dokl. Akad. Nauk S. S. S. R. 11., 831 (1956).

    CAS  Google Scholar 

  • Kochetko., N. K., E. I. Budovski., R. M. Khomuto., and M. YA. Karpeiski.: Cycloserine and related compounds. V. Cyclization of alpha-benzoylamino-betaarylacrylohydroxamic acids. J. Gen. Chem. (U.S.S.R.) 2., 630 (1959).

    Google Scholar 

  • Kolesinsk., J.: Cycloserine stability at various temperatures and pH values. Med. Doswiadczalna i. Mikrobiol. 1., 189 (1961)

    CAS  Google Scholar 

  • Kolesinsk., J.: Cycloserine stability at various temperatures and pH values. Chem. Abstr. 5., 24883 (1961).

    Google Scholar 

  • Kotschetko., N. K.: Die Chemie des Antibiotikums Cykloserin. Österr. ChemikerZtg. 6., 276 (1961).

    Google Scholar 

  • Kueh., F. A., F. J. Wol., N. R. Trenne., R. L. Pec., E. How., B. D. Hunn.-Wel., G. Downin., E. Newstea., R. P. B.HS, I. Putte., R. Ormon., J. E. Lyon., L. Chale., and K. Folker.: D-4-Amino-3-isoxazolidone, a new antibiotic. J. Am. Chem. Soc. 7., 2344 (1955).

    CAS  Google Scholar 

  • Kurihar., T., and K. Chib.: Orientomycin, a new antibiotic. Ann. Rept. Tohoku coil. Pharm., 83 (1956)

    Google Scholar 

  • Kurihar., T., and K. Chib.: Orientomycin, a new antibiotic. Chem. Abstr. 5., 5197 (1957).

    Google Scholar 

  • Lar., C., and R. Schichte.: Comparison of spheroplast induction in Alcaligenes faecali. by three different agents. J. Bacteriol. 8., 1241 (1962).

    PubMed  CAS  Google Scholar 

  • Leste., W., A. Salomi., A. F. Reiman., E. Shulruf., and G. S. Ger.: Cycloserine therapy in tuberculosis in humans. Am. Rev. Tuberc. 7., 121 (1956).

    PubMed  Google Scholar 

  • Lillic., L., R. Stran., L. J. Boy., M. Schwimme., and M. G. Mulino.: Cycloserine in the treatment of nontuberculosis infections. Antibiotics Ann. 1955/5., 158.

    Google Scholar 

  • Longenecke., J. B., and E. E. Snel.: Pyridoxal and metal ion catalysis of alphabeta-elimination reactions of serine-3-phosphate and related compounds. J. Biol. Chem. 22., 409 (1957).

    PubMed  CAS  Google Scholar 

  • Lync., J. L., and F. C. Neuhau.: On the mechanism of action of the antibiotic O-carbamyl-D-serine in Streptococcus faecali. R. J. Bacteriol. 9., 449 (1966).

    PubMed  CAS  Google Scholar 

  • Malam., M. H., and B. L. Horecke.: Release of alkaline phosphates from cells of Escherichia col. upon lysozyme spheroplast formation. Biochemistry., 1889 (1964).

    PubMed  CAS  Google Scholar 

  • Martine.-Carrio., M., and W. T. Jenkin.: D-Alanine-D-glutamiC transaminase. II. Inhibitors and the mechanism of transamination of D-amino acids. J. Biol. Chem. 24., 3547 (1965).

    Google Scholar 

  • Meado., P. M., J. S. Anderso., and L. Strominge.: Enzymatic polymerization of UDP-acetylmuramyl-L-ala-D-glu-L-lys-D-ala-D-ala and UDP-acetylglucosamine by a particulate enzyme from Staphylococcus aureu. and its inhibition by antibiotics. Biochem. Biophys. Research Commun. 1., 382 (1964).

    CAS  Google Scholar 

  • Michalsk., J., J. Opicha. U. J. ÔTvrtni.: Cycloserin und verwandte Verbindungen; Über die Kondensationsprodukte von D,L-4-Amino-3-isoxazolidon und 2,5-Bis(aminooxymethyl)-3,6-diketopiperazin. Monatsh. Chem. 9., 618 (1962a).

    CAS  Google Scholar 

  • Michals.Ý, J., J. ČTvrtni., Z. HoKo.Á U. V. ByOvs.Ý: Über die tuberkulostatische Aktivität von 2,5-Bis-(aminoxymethyl)-3,6-diketopiperazin, eines Umwandlungsproduktes des Cyclo serins Experientia. 1., 217 (1962b).

    Google Scholar 

  • Miche., M. F., and W. Human.: The additive effect of glycine and other amino acids on the induction of the L-phase of group A beta-haemolytic streptococci by penicillin and D-cycloserine. J. Gen. Microbiol. 2., 35 (1960).

    CAS  Google Scholar 

  • Mor., J., and L. F. Bojali.: Antagonism of the D-alanine reversal of D-cycloserine action by L-alanine in Mycobacterium acapulcensi Proc. Soc. Exptl. Biol. Med. 11., 49 (1965).

    CAS  Google Scholar 

  • Mor., J., and E. E. Snel.: The uptake of amino acids by cells and protoplasts of Streptococcus faecali Biochemistry., 136 (1963).

    CAS  Google Scholar 

  • Morriso., N. E.: The reversal of D-cycloserine inhibition of mycobacterial growth. Bacteriol. Proc. 86 (1962).

    Google Scholar 

  • Moulde., J. W., D. L. Novose., and J. E. Office.: Inhibition of the growth of agents of the psittacosis group by D-cycloserine and its specific reversal by D-alanine J. Bacteriol. 8., 707 (1963).

    Google Scholar 

  • Moulde., J. W., D. L. Novose., and I. I. E. Tribb.: Changes in mouse pneumonitis agent associated with development of resistance to chlortetracycline. J. Bacteriol. 8., 17 (1965).

    PubMed  CAS  Google Scholar 

  • Mope., H. S.: Biochemical mechanisms of drug resistance. Ann. Rev. Microbiol. 1., 247 (1964).

    Google Scholar 

  • Muli.os, M. G.: Cycloserine: An antibiotic paradox. Antibiotics Ann. 1955/5., 131.

    Google Scholar 

  • Murar., G., G. Salgarell., and R. Moratell.: Antibacterial activity of optical isomers of cycloserine and of its synthetic intermediate (isoxazolidone). Action on Escherichia col. and Salmonell Boll. soc. ital. biol. sper. 3., 1534 (1958)

    PubMed  CAS  Google Scholar 

  • Murar., G., G. Salgarell., and R. Moratell.: Antibacterial activity of optical isomers of cycloserine and of its synthetic intermediate (isoxazolidone). Action on Escherichia col. and Salmonell Chem. Abstr. 5., 14583 (1961).

    Google Scholar 

  • Nakamur., M.: Amebacidal action of cycloserine. Experientia 1., 29 (1957).

    CAS  Google Scholar 

  • Neiland., J. B.: Metal and hydrogen-ion binding properties of cycloserine. Arch. Biochem. Biophys. 6., 151 (1956).

    PubMed  CAS  Google Scholar 

  • Neuhau., F. C., and W. G. Strov.: Enzymatic synthesis of analogs of the cell-wall precursor. I. Kinetics and specificity of uridine diphospho-N-acetyl-muramylL-alanyl-D-glutamyl-L-lysine: D-Alanyl-D-alanine ligase (adenosine diphosphate) from Streptococcus faecali. R. Biochemistry., 120 (1965).

    PubMed  CAS  Google Scholar 

  • Neuhau., F. C.: The enzymatic synthesis of D-alanyl-D-alanine I Purification and properties of D-alanyl-D-alanine synthetase. J. Biol. Chem. 23., 778 (1962a).

    PubMed  CAS  Google Scholar 

  • Neuhau., F. C.: The enzymatic synthesis of D-alanyl-D-alanine. II. Kinetic studies of D-alanyl-D-alanine synthetase. J. Biol. Chem. 23., 3128 (1962b).

    PubMed  CAS  Google Scholar 

  • Neuhau., F. C., and J. L. Lync.: The enzymatic synthesis of D-alanyl-D-alanine. Ii On the inhibition of D-alanyl-D-alanine synthetase by the antibiotic D-cycloserine. Biochemistry., 471 (1964).

    PubMed  CAS  Google Scholar 

  • Nitt., V., and M. Tsukamur.: Resistance of tuberculosis mycobacteria to cycloserine in vitr Arch. tisiol. mal. app. respirat. (Naples) 1., 71 (1957)

    CAS  Google Scholar 

  • Nitt., V., and M. Tsukamur.: Resistance of tuberculosis mycobacteria to cycloserine in vitr Chem. Abstr. 5., 13069 (1957).

    Google Scholar 

  • Okam., Y., K. Maed., H. Kond., T. Tanak., and H. Umezaw.: A streptomyces producing O-carbamyl-D-serine. J. Antibiotics (Japan), Ser. A 1., 147 (1962).

    CAS  Google Scholar 

  • Par., J. T.: Selective inhibition of bacterial cell-wall synthesis: Its possible applications in chemotherapy. Symp. Soc. Gen. Microbiol., 49 (1958a).

    Google Scholar 

  • Par., J. T.: Inhibition of cell-wall synthesis in Staphylococcus aureu. by chemicals which cause accumulation of wall precursors. Biochem. J. 7., 2 P (1958b).

    Google Scholar 

  • Par., J. T.: Inhibition of synthesis of bacterial mucopeptide or protein by certain antibiotics and its possible significance for microbiology and medicine. Antimicrobial Agents Ann. 338 (1960).

    Google Scholar 

  • Par., J. T., and R. Hancoc.: A fractionation procedure for studies of the synthesis of cell-wall mucopeptide and of other polymers in cells of Staphylococcus aureu J. Gen. Microbiol. 2., 249 (1960).

    PubMed  CAS  Google Scholar 

  • Paskhin., T. S.: Effect of isomers of cycloserine on the activity of D-alanine-D-glutamic transaminase of Bacillus subtili Voprosy Med. Khim. 1., 526 (1964)

    CAS  Google Scholar 

  • Paskhin., T. S.: Effect of isomers of cycloserine on the activity of D-alanine-D-glutamic transaminase of Bacillus subtili Chem. Abstr. 5., 2978 (1965).

    Google Scholar 

  • Patnod., R. A., P. C. Hudgin., and M. M. Cumming.: Effect of cycloserine on experimental tuberculosis in guinea pigs. Am. Rev. Tuberc. Pulmonary Diseases 7., 117 (1955).

    CAS  Google Scholar 

  • Pepinsk., R.: X-Rays and the absolute configuration of optically active molecules. Record Chem. Progr. 1., 145 (1956).

    CAS  Google Scholar 

  • Perr., D., and H. D. Slad.: Intraspecific and interspecific tranformation in Streptococci. J. Bacteriol. 8., 595 (1964).

    PubMed  CAS  Google Scholar 

  • Pietr., G. D., F. Delorenz., and G. Illian.: Biochim. Appl. 1., 123 (1963)

    CAS  Google Scholar 

  • F. Cedrangol., in E. E. Snel., P. M. Fasell., A. E. Braunstei., and A. Ross.-Fanell. (editors), Chemical and Biological Aspects of Pyridoxal Catalysis, p. 343. NewYork: Pergamon Press 1963.

    Google Scholar 

  • Pittill., R. F., and J. W. Foste.: Potentiation of Inhibitor action through determination of reversing metabolites. J. Bacteriol. 6., 53 (1953).

    Google Scholar 

  • Plap., R., u. O. Kandle.: Zur Wirkung zellwandhemmender Antibiotica bei gram-negativen Bakterien. II. Die Wirkung von D-Cycloserin auf die Konzentration von Zellwandvorstufen in Proteus mirabili. und dessen L-Phase. Arch. Mikrobiol. 5., 282 (1965).

    PubMed  CAS  Google Scholar 

  • Pohlan., A.: 3-Isoxazolidones, derivatives and process. U.S. Patent 2,762,815 (September 11, 1956 ).

    Google Scholar 

  • Polyanovski., O. L., and Y. M. Torchinski.: Effect of cycloserine and of related substances on the activity of pig-heart aspartate-glutamate transaminase and alanine-glutamic transaminase Doklady Akad. Nauk S.S. S.R. 14., 488 (1961).

    CAS  Google Scholar 

  • Plattne., PL. A., A. Bolle., H. Fric., A. FÜRs., B. Hege.ÜS, H. Kirchensteine., ST. Majnon., R. SchPfe. u. H. Spiegelber.: Synthesen des 4-Amino3-isoxazolidinons (Cycloserin) und einiger Analoga. Helv. Chim. Acta 4., 1531 (1957).

    CAS  Google Scholar 

  • Ratoui., R., and R. Beha.: Synthesis of 4-amino-3-isoxazolidinone. Bull. soc. chim. France 195., 1255.

    Google Scholar 

  • Reit., R., H. D. Slad., and F. C. Neuhau.: On the biochemical basis of D-cycloserine resistance. Federation Proc. Abstracts 2., 344 (1966).

    Google Scholar 

  • Robso., J. M., and F. M. Sulliva.: Antituberculosis drugs. Pharmacol. Rev. 1., 195 (1963).

    Google Scholar 

  • Roger., H. J., and A. J. Garret.: The interrelationship between mucopeptide and ribitol teichoic acid formation as shown by the effect of inhibitors. Biochem. J. 9., 231 (1965).

    PubMed  CAS  Google Scholar 

  • Roz., U.: The non-enzymatic reaction between cycloserine and pyridoxal phosphate. Ph. D. Thesis, submitted to the graduate school of Washington University, St. Louis Missouri 1964.

    Google Scholar 

  • Roz., U., and J. L. Strominge.: The non-enzymatic reaction between D-cycloserine and pyridoxal phosphate. Federation Proc. Abstracts 2., 423 (1963).

    Google Scholar 

  • Roz., U., and J. L. Strominge.: Alanine racemase from Staphylococcus aureu.: Conformation of its substrates and its inhibitor; D-cycloserine. J. Mol. Pharmacol., 92 (1966).

    CAS  Google Scholar 

  • Rung., W. F.: Process of producing acetyl cycloserine. U.S. Patent 2,815,348 (December 3, 1957 ).

    Google Scholar 

  • Russel., W. F. Jr., and G. Middlebroo.: Chemotherapy of tuberculosis. Springfield (Ill.): Ch. C. Thomas 1961.

    Google Scholar 

  • Sait., M., N.Ishimot., and E. It.: Uridine diphosphate N-acetylamino sugar derivatives in penicillin-treated Staphylococcus aureu J. Biochemistry (Tokyo) 5., 273 (1963).

    CAS  Google Scholar 

  • Salgarell., G., and E. Turr.: Antibacterial activity of optical isomers of cycloserine. Action on Mycobacterium tuberculosi Boll. soc. ital. biol. sper. 3., 1538 (1958)

    PubMed  CAS  Google Scholar 

  • Salgarell., G., and E. Turr.: Antibacterial activity of optical isomers of cycloserine. Action on Mycobacterium tuberculosi Chem. Abstr. 5., 14583 (1961).

    Google Scholar 

  • Salto., M. R. J.: The anatomy of the bacterial surface. Bacteriol. Rev. 2., 77 (1961).

    PubMed  CAS  Google Scholar 

  • Salto., M. R. J.: The Bacterial Cell Wall, p. 107. Amsterdam: Elsevier Publ. Co. 1964.

    Google Scholar 

  • Saukkone., J., and P. Virkol.: Acid-soluble nucleotides of Staphylococcus aureu Ann. Med. Exptl. et Biol. Fenniae (Helsinki) 4., 220 (1963).

    CAS  Google Scholar 

  • Seremb., M.: Antituberculous action of levorotatory and dextrorotatory cycloserine and of some synthetic intermediates. Minerva med. 1957, 3548

    Google Scholar 

  • Seremb., M.: Antituberculous action of levorotatory and dextrorotatory cycloserine and of some synthetic intermediates. Chem. Abstr. 5., 18837 (1958).

    Google Scholar 

  • Shockma., G. D.: Reversal of cycloserine inhibition by D-alanine Proc. Soc. Exptl. Biol. Med. 10., 693 (1959).

    CAS  Google Scholar 

  • Shockma., G. D., and J. O. Lampe.: Inhibition by antibiotics of the growth of bacterial and yeast protoplasts. J. Bacteriol. 8., 508 (1962).

    PubMed  CAS  Google Scholar 

  • Shul., G. M., and J. L. Sardina.: PA-94, an antibiotic identical with D-4-amino3-isoxazolidinone (cycloserine, oxamycin). Antibiotics & Chemotherapy., 398 (1955).

    CAS  Google Scholar 

  • Shul., G. M., J. B. Routie., and A. C. Finla.: Cycloserine and production there of. U.S. Patent., 773, 878 (December 11, 1956 ).

    Google Scholar 

  • Skinne., C. G., T. J. Mccor., J. M. Rave., and W. Shiv.: O-Carbamyl-L-serine, an inhibitory analog of L-glutamine. J. Am. Chem. Soc. 7., 2412 (1955).

    Google Scholar 

  • Smit., J. L., and E. D. Weinber.: Mechanisms of antibacterial action of bacitracin. J. Gen. Microbiol. 2., 559 (1962).

    PubMed  CAS  Google Scholar 

  • Smr., J., J. Berane., J. Siche., and F. Som.: Synthesa 4-amino-3-isoxazolidinonu (cykloserinu). Chem. listy 5., 112 (1957a).

    CAS  Google Scholar 

  • Smr., J., J. Berane., J. Siche., J. Skod., V. F. Hes., and F. Sor.: Synthesis of L-4-amino-3-isoxazolidinone, the unnatural stereoisomer of cycloserine and its antibiotic activity. Experientia 1., 291 (1957 b).

    Google Scholar 

  • Sho., G. A.: Structure of mycobactin. Biochem. J. 9., 166 (1965).

    Google Scholar 

  • Stamme., C. H.: Beta-Aminoxy-D-alanine. J. Org. Chem. 2., 2957 (1962).

    CAS  Google Scholar 

  • Stamme., C. H., and J. D. Mckinne.: Cycloserine. Ii A schiff base and its reactions. J. Org. Chem. 3., 3436 (1965).

    PubMed  CAS  Google Scholar 

  • Stamme., C. H., A. N. Wilso., C. F. Spence., F. W. Bachelo., F. W. Holl., and K. Folker.: Synthesis of D-4-amino-3-isoxazolidone. J. Am. Chem. Soc. 7., 3236 (1957).

    CAS  Google Scholar 

  • Stamme., C. H., A. N. Wilso., F. W. Holl., and K. Folker.: Synthesis of D-4-amino-3-isoxazolidone. J. Am. Chem. Soc. 7., 2346 (1955).

    CAS  Google Scholar 

  • Steenke., W. JR., and E. Wolinsk.: Cycloserine: Antituberculous activity in vitr. and in the experimental animal. Am. Rev. Tuberc. Pulmonary Diseases 7., 539 (1956).

    CAS  Google Scholar 

  • Strominge., J. L.: Biosynthesis of bacterial cell walls. Federation Proc. 21, 134 (1962).

    CAS  Google Scholar 

  • Strominge., J. L., R. H. Thren., and S. S. Scot.: Oxamycin, a competitive antagonist of the incorporation of D-alanine into a uridine nucleotide in Staphylococcus aureu J. Am. Chem. Soc. 8., 3803 (1959).

    CAS  Google Scholar 

  • Strominge., J. L., E. It., and R. H. Thren.: Competitive inhibition of enzymatic reactions by oxamycin. J. Am. Chem. Soc. 8., 998 (1960).

    CAS  Google Scholar 

  • Strominge., J. L., J. T. Par., and R. E. Thompso.: Composition of the cell wall of Staphylococcus aureu.: Its relation to the mechanism of action of penicillin. J. Biol. Chem. 23., 3263 (1959).

    PubMed  CAS  Google Scholar 

  • Struv., W. G., and F. C. Neuhau.: Evidence for an initial acceptor of UDP-NAcmuramyl-pentapeptide in the synthesis of bacterial mucopeptide. Biochem. Biophys. Research Commun. 1., 6 (1965).

    CAS  Google Scholar 

  • Struv., W. G., R. K. Sinh., and F. C. Neuhau.: On the initial stage in peptidoglycan synthesis. Phospho-N-acetyl-muramyl-pentapeptide translocase (uridine monophosphate). Biochemistry., 82 (1966).

    PubMed  CAS  Google Scholar 

  • Sutto., W. B., and L. Stanfiel.: The reversal of cycloserine inhibition by mycobactin, a growth factor for mycobacteria. Antibiotics & Chemotherapy., 582 (1955).

    CAS  Google Scholar 

  • Tanak., N.: Mechanism of action of O-carbamyl-D-serine, a new member of cell wall synthesis inhibitors. Biochem. Biophys. Research Commun. 1., 68 (1963).

    CAS  Google Scholar 

  • Tanak., N., and K. Sashikat.: Biogenesis of D-4-amino-3-isoxazolidone and O-carbamyl-D-serine. J. Gen Appl. Microbiol., 409 (1963).

    CAS  Google Scholar 

  • Tanak., N., K. Sashikat., T. Wad., S. Sugawar., and H. Umezaw.: Mechanism of action of O-carbamyl-D-serine. J. Antibiotics, Ser. A 1., 217 (1963).

    CAS  Google Scholar 

  • Tanak., N., and H. Umezaw.: Synergism of D-4-amino-3-isoxazolidone and O-carbamyl-D-serine. J. Antibiotics, Ser. A 1., 8 (1964).

    CAS  Google Scholar 

  • Toennie., G., and G. D. Shockma.: Growth chemistry of Streptococcus faecali Proceedings of the fourth internat. Congr. of Biochemistry, vol. 13, p. 365. London: Pergamon Press 1959.

    Google Scholar 

  • Trivellat., E.: Stereoisomers of cycloserine. II. Activity against Escherichia col. in synthetic media. Arch. intern. pharmacodynamie 11., 317 (1958).

    CAS  Google Scholar 

  • Trivellat., E., and C. Concili.: Stereoisomers of cycloserine. I. Bacteriostatic activity towards some microorganisms. Arch. intern. pharmacodynamie 11., 313 (1958)

    CAS  Google Scholar 

  • Trivellat., E., and C. Concili.: Stereoisomers of cycloserine. I. Bacteriostatic activity towards some microorganisms. Chem. Abstr. 5., 12392 (1959).

    Google Scholar 

  • Viallie., J., and R. M. Cay.É: Bacilles tuberculeus résistants à la cyclosérine. Compt. rend. soc. biol. 15., 776 (1958).

    CAS  Google Scholar 

  • Vyshepa., E. D., K. I. Ivanov., and A. M. Chernuk.: Inhibition of glutamicpyruvic transaminase. Byull. Eksptl. Biol. Med. 5., 76 (1961).

    CAS  Google Scholar 

  • Vyshepa., E. D., K. I. Ivanov., and A. M. Chernuk.: The effect of D,L-cycloserine on the process of transamination. Byull. Eksptl. Biol. Med. 4., 52 (1959).

    CAS  Google Scholar 

  • Weinber., E. D.: The mutual effects of antimicrobial compounds and metallic cations. Bacteriol. Rev. 2., 46 (1957).

    PubMed  CAS  Google Scholar 

  • Wishno., R. M., J. L. Strominge., C. H. Birg., and R. H. Thren.: Biochemical effects of novobiocin on Staphylococcus aureu J. Bacteriol. 8., 1117 (1965).

    PubMed  CAS  Google Scholar 

  • Woo., W. A., and I. C. Gunsalu.: D-Alanine formation: A racemase in Streptococcus faecali J. Biol. Chem. 19., 403 (1951).

    PubMed  CAS  Google Scholar 

  • Yamad., K., S. Sawak., and S. Hayam.: Inhibitory effect of cycloserine on some enzymic activities related to vitamin Br. J. Vitaminol (Osaka) 3., 68 (1957).

    CAS  Google Scholar 

  • Youman., G. P., and A. S. Youman.: Experimental chemotherapy of tuberculosis and other mycobacterial infections. In: R. J. Schnitze. and F. Hawkin. (editors), Experimental Chemotherapy, vol. II, p. 393. NewYork: Academic Press 1964.

    Google Scholar 

  • Zygmun., W. A.: Reversal of D-cycloserine inhibition of bacterial growth by alanine J. Bacteriol. 84., 154 (1962).

    PubMed  CAS  Google Scholar 

  • Zygmun., W. A.: Antagonism of D-cycloserine inhibition of mycobacterial growth by D-alanine J Bacteriol. 85., 1217 (1963).

    CAS  Google Scholar 

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Neuhaus, F.C. (1967). D-Cycloserine and O-Carbamyl-D-serine. In: Gottlieb, D., Shaw, P.D. (eds) Antibiotics. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-38439-8_3

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