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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
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).
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).
Aok., T.: The mode of action of cycloserine. II. The influence on glutamic-aspartic transamination. Kekkaku 3., 544 (1957)
Aok., T.: The mode of action of cycloserine. II. The influence on glutamic-aspartic transamination. Chem. Abstr. 5., 7427 (1958).
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)
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).
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).
Bonavit., V.: Purification and properties of glutamic-oxaloacetic transaminase from human brain. J. Neurochem., 275 (1959).
Bond., A., J. Kornblu., and C. Fort.: Inhibition of antibacterial activity of cycloserine by alpha-alanine. Proc. Soc. Exptl. Biol. Med. 9., 270 (1957).
Botter., A., G. Pern., G. C. Colomb., and F. Leid.: Experimental and clinical studies on cycloserine resistance. Giorn. ital. tuberc. 1., 10 (1958).
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.
Braunstei., A. E., R. M. Azark., and T. A. Syu.: Kinetics of inhibition of transaminases by cycloserine. Biokhimiya 2., 882 (1961)
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).
Brettschneide., H., u. W. Vette.: Synthese des DL-4-Amino-3-isoxazOlidofs sowie seiner D-Form, des natürlichen Cycloserins. Monatsh. Chem. 9., 799 (1959).
Brettschneide., H., W. Vette. u. E. Semenit.: Synthese und antibakterielle Eigenschaften des D,L-N,N-Dimethylcycloserins. Monatsh. Chem. 8., 627 (1958).
Brege., M. A.: The biological activity of cycloserine and some of its analogues and homologues. Antibiotiki, 26 (1961).
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);
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).
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).
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).
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).
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).
Com., D. G.: The enzymatic addition of D-alanyl-D-alanine to a uridine nucleotide-peptide. J. Biol. Chem. 23., 1601 (1962).
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).
Cumming., M. M., R. A. Patnod., and P. C. Hudgin.: Effects of cycloserine on Mycobacterium tuberculosis in vitr Antibiotics & Chemotherapy., 198 (1955).
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).
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).
Dan., O. T., and C. E. Carte.: Cycloserine inhibition of gamma-aminobutyric-alphaketoglutaric transaminase. Biochem. Pharmacology 1., 677 (1964).
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).
Demere., M.: Origin of bacterial resistance to antibiotics. J. Bacteriol. 5., 63 (1948).
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).
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).
Fet., T., and K. Kazi.: In vitr. action of cycloserine on Mycobacterium tuberculosi Bacteriol. Proc. 85 (1962).
Folker., K.: 4-Pyridoxylamino-3-isoxazolidone compounds. U.S. Patent., 776, 296 (January 1, 1957 ).
Freckin., M. G., and P. D. Hoepric.: Effect of cycloserines on D-amino acid oxidase. Arch. Biochem. Biophys. 11., 108 (1966).
Frees., E., and J. Oosterwy.: The induction of alanine dehydrogenase. Biochemistry., 1212 (1963).
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).
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).
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).
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).
Hah., F. E., and J. Cia.: Penicillin-induced lysis of Escherichia col Science 12., 119 (1957).
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).
Harne., R. L., P. H. Hid., and E. K. LA Ba.: Cycloserine. I. A preliminary report. Antibiotics & Chemotherapy., 204 (1955).
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).
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 ).
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).
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).
Hodg., E. B.: Substituted cycloserines. U.S. Patent 2,971,004 (February 7, 1961 ).
Hodg., E. B.: N-(p-Chlorobenzyl)-cycloserine. U.S. Patent 2,967,866 (January 10, 1961 ).
Hoepric., P. D.: Alanine: Cycloserine antagonism. Ii Quantitative aspects and relations to heating of culture media. J. Lab. Clin. Med. 6., 657 (1963).
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).
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 ).
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).
Ikaw., M., and E. E. Snel.: Cell wall composition of lactic acid bacteria. J. Biol. Chem. 23., 1376 (1960).
Ishi., K., and M. G. Seva.: Inhibition by cycloserine of the synthesis of 5-amino-4-imidazolecarboxamide by Escherichia col Antibiotics & Chemotherapy., 500 (1956).
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).
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).
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).
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).
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.
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)
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).
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).
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).
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)
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).
Khomuto., R. M., M. YA. Karpeiski., and E. S. Severi.: The relationship between biological activity and chemical properties. Biokhimiya 2., 772 (1961)
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).
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).
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.
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).
Kochetko., N. K., R. M. Khomuto., and M. YA. Karpeiski.: New synthesis of cycloserine. Dokl. Akad. Nauk S. S. S. R. 11., 831 (1956).
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).
Kolesinsk., J.: Cycloserine stability at various temperatures and pH values. Med. Doswiadczalna i. Mikrobiol. 1., 189 (1961)
Kolesinsk., J.: Cycloserine stability at various temperatures and pH values. Chem. Abstr. 5., 24883 (1961).
Kotschetko., N. K.: Die Chemie des Antibiotikums Cykloserin. Österr. ChemikerZtg. 6., 276 (1961).
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).
Kurihar., T., and K. Chib.: Orientomycin, a new antibiotic. Ann. Rept. Tohoku coil. Pharm., 83 (1956)
Kurihar., T., and K. Chib.: Orientomycin, a new antibiotic. Chem. Abstr. 5., 5197 (1957).
Lar., C., and R. Schichte.: Comparison of spheroplast induction in Alcaligenes faecali. by three different agents. J. Bacteriol. 8., 1241 (1962).
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).
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.
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).
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).
Malam., M. H., and B. L. Horecke.: Release of alkaline phosphates from cells of Escherichia col. upon lysozyme spheroplast formation. Biochemistry., 1889 (1964).
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).
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).
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).
Michals.Ý, J., J. ČTvrtni., Z. Ho.ÁKo.Á U. V. By.ŽOvs.Ý: Über die tuberkulostatische Aktivität von 2,5-Bis-(aminoxymethyl)-3,6-diketopiperazin, eines Umwandlungsproduktes des Cyclo serins Experientia. 1., 217 (1962b).
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).
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).
Mor., J., and E. E. Snel.: The uptake of amino acids by cells and protoplasts of Streptococcus faecali Biochemistry., 136 (1963).
Morriso., N. E.: The reversal of D-cycloserine inhibition of mycobacterial growth. Bacteriol. Proc. 86 (1962).
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).
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).
Mope., H. S.: Biochemical mechanisms of drug resistance. Ann. Rev. Microbiol. 1., 247 (1964).
Muli.os, M. G.: Cycloserine: An antibiotic paradox. Antibiotics Ann. 1955/5., 131.
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)
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).
Nakamur., M.: Amebacidal action of cycloserine. Experientia 1., 29 (1957).
Neiland., J. B.: Metal and hydrogen-ion binding properties of cycloserine. Arch. Biochem. Biophys. 6., 151 (1956).
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).
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).
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).
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).
Nitt., V., and M. Tsukamur.: Resistance of tuberculosis mycobacteria to cycloserine in vitr Arch. tisiol. mal. app. respirat. (Naples) 1., 71 (1957)
Nitt., V., and M. Tsukamur.: Resistance of tuberculosis mycobacteria to cycloserine in vitr Chem. Abstr. 5., 13069 (1957).
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).
Par., J. T.: Selective inhibition of bacterial cell-wall synthesis: Its possible applications in chemotherapy. Symp. Soc. Gen. Microbiol., 49 (1958a).
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).
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).
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).
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)
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).
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).
Pepinsk., R.: X-Rays and the absolute configuration of optically active molecules. Record Chem. Progr. 1., 145 (1956).
Perr., D., and H. D. Slad.: Intraspecific and interspecific tranformation in Streptococci. J. Bacteriol. 8., 595 (1964).
Pietr., G. D., F. Delorenz., and G. Illian.: Biochim. Appl. 1., 123 (1963)
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.
Pittill., R. F., and J. W. Foste.: Potentiation of Inhibitor action through determination of reversing metabolites. J. Bacteriol. 6., 53 (1953).
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).
Pohlan., A.: 3-Isoxazolidones, derivatives and process. U.S. Patent 2,762,815 (September 11, 1956 ).
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).
Plattne., PL. A., A. Bolle., H. Fric., A. FÜRs., B. Hege.ÜS, H. Kirchensteine., ST. Majnon., R. Sch.ÄPfe. u. H. Spiegelber.: Synthesen des 4-Amino3-isoxazolidinons (Cycloserin) und einiger Analoga. Helv. Chim. Acta 4., 1531 (1957).
Ratoui., R., and R. Beha.: Synthesis of 4-amino-3-isoxazolidinone. Bull. soc. chim. France 195., 1255.
Reit., R., H. D. Slad., and F. C. Neuhau.: On the biochemical basis of D-cycloserine resistance. Federation Proc. Abstracts 2., 344 (1966).
Robso., J. M., and F. M. Sulliva.: Antituberculosis drugs. Pharmacol. Rev. 1., 195 (1963).
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).
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.
Roz., U., and J. L. Strominge.: The non-enzymatic reaction between D-cycloserine and pyridoxal phosphate. Federation Proc. Abstracts 2., 423 (1963).
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).
Rung., W. F.: Process of producing acetyl cycloserine. U.S. Patent 2,815,348 (December 3, 1957 ).
Russel., W. F. Jr., and G. Middlebroo.: Chemotherapy of tuberculosis. Springfield (Ill.): Ch. C. Thomas 1961.
Sait., M., N.Ishimot., and E. It.: Uridine diphosphate N-acetylamino sugar derivatives in penicillin-treated Staphylococcus aureu J. Biochemistry (Tokyo) 5., 273 (1963).
Salgarell., G., and E. Turr.: Antibacterial activity of optical isomers of cycloserine. Action on Mycobacterium tuberculosi Boll. soc. ital. biol. sper. 3., 1538 (1958)
Salgarell., G., and E. Turr.: Antibacterial activity of optical isomers of cycloserine. Action on Mycobacterium tuberculosi Chem. Abstr. 5., 14583 (1961).
Salto., M. R. J.: The anatomy of the bacterial surface. Bacteriol. Rev. 2., 77 (1961).
Salto., M. R. J.: The Bacterial Cell Wall, p. 107. Amsterdam: Elsevier Publ. Co. 1964.
Saukkone., J., and P. Virkol.: Acid-soluble nucleotides of Staphylococcus aureu Ann. Med. Exptl. et Biol. Fenniae (Helsinki) 4., 220 (1963).
Seremb., M.: Antituberculous action of levorotatory and dextrorotatory cycloserine and of some synthetic intermediates. Minerva med. 1957, 3548
Seremb., M.: Antituberculous action of levorotatory and dextrorotatory cycloserine and of some synthetic intermediates. Chem. Abstr. 5., 18837 (1958).
Shockma., G. D.: Reversal of cycloserine inhibition by D-alanine Proc. Soc. Exptl. Biol. Med. 10., 693 (1959).
Shockma., G. D., and J. O. Lampe.: Inhibition by antibiotics of the growth of bacterial and yeast protoplasts. J. Bacteriol. 8., 508 (1962).
Shul., G. M., and J. L. Sardina.: PA-94, an antibiotic identical with D-4-amino3-isoxazolidinone (cycloserine, oxamycin). Antibiotics & Chemotherapy., 398 (1955).
Shul., G. M., J. B. Routie., and A. C. Finla.: Cycloserine and production there of. U.S. Patent., 773, 878 (December 11, 1956 ).
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).
Smit., J. L., and E. D. Weinber.: Mechanisms of antibacterial action of bacitracin. J. Gen. Microbiol. 2., 559 (1962).
Smr., J., J. Berane., J. Siche., and F. Som.: Synthesa 4-amino-3-isoxazolidinonu (cykloserinu). Chem. listy 5., 112 (1957a).
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).
Sho., G. A.: Structure of mycobactin. Biochem. J. 9., 166 (1965).
Stamme., C. H.: Beta-Aminoxy-D-alanine. J. Org. Chem. 2., 2957 (1962).
Stamme., C. H., and J. D. Mckinne.: Cycloserine. Ii A schiff base and its reactions. J. Org. Chem. 3., 3436 (1965).
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).
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).
Steenke., W. JR., and E. Wolinsk.: Cycloserine: Antituberculous activity in vitr. and in the experimental animal. Am. Rev. Tuberc. Pulmonary Diseases 7., 539 (1956).
Strominge., J. L.: Biosynthesis of bacterial cell walls. Federation Proc. 21, 134 (1962).
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).
Strominge., J. L., E. It., and R. H. Thren.: Competitive inhibition of enzymatic reactions by oxamycin. J. Am. Chem. Soc. 8., 998 (1960).
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).
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).
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).
Sutto., W. B., and L. Stanfiel.: The reversal of cycloserine inhibition by mycobactin, a growth factor for mycobacteria. Antibiotics & Chemotherapy., 582 (1955).
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).
Tanak., N., and K. Sashikat.: Biogenesis of D-4-amino-3-isoxazolidone and O-carbamyl-D-serine. J. Gen Appl. Microbiol., 409 (1963).
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).
Tanak., N., and H. Umezaw.: Synergism of D-4-amino-3-isoxazolidone and O-carbamyl-D-serine. J. Antibiotics, Ser. A 1., 8 (1964).
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.
Trivellat., E.: Stereoisomers of cycloserine. II. Activity against Escherichia col. in synthetic media. Arch. intern. pharmacodynamie 11., 317 (1958).
Trivellat., E., and C. Concili.: Stereoisomers of cycloserine. I. Bacteriostatic activity towards some microorganisms. Arch. intern. pharmacodynamie 11., 313 (1958)
Trivellat., E., and C. Concili.: Stereoisomers of cycloserine. I. Bacteriostatic activity towards some microorganisms. Chem. Abstr. 5., 12392 (1959).
Viallie., J., and R. M. Cay.É: Bacilles tuberculeus résistants à la cyclosérine. Compt. rend. soc. biol. 15., 776 (1958).
Vyshepa., E. D., K. I. Ivanov., and A. M. Chernuk.: Inhibition of glutamicpyruvic transaminase. Byull. Eksptl. Biol. Med. 5., 76 (1961).
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).
Weinber., E. D.: The mutual effects of antimicrobial compounds and metallic cations. Bacteriol. Rev. 2., 46 (1957).
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).
Woo., W. A., and I. C. Gunsalu.: D-Alanine formation: A racemase in Streptococcus faecali J. Biol. Chem. 19., 403 (1951).
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).
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.
Zygmun., W. A.: Reversal of D-cycloserine inhibition of bacterial growth by alanine J. Bacteriol. 84., 154 (1962).
Zygmun., W. A.: Antagonism of D-cycloserine inhibition of mycobacterial growth by D-alanine J Bacteriol. 85., 1217 (1963).
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1967 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
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
Download citation
DOI: https://doi.org/10.1007/978-3-662-38439-8_3
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-37649-2
Online ISBN: 978-3-662-38439-8
eBook Packages: Springer Book Archive