D-Cycloserine and O-Carbamyl-D-serine

  • Francis C. Neuhaus
Part of the Antibiotics book series (ANTIBIOTICS, volume 1)

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.

Keywords

Schiff Base Mycobacterium Tuberculosis Pyridoxal Phosphate Alcaligenes Faecalis Alanine Racemase 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Alioto, M. R.: In vitro and in vivo action of cycloserine on L-alanine-alpha-ketoglutaric transaminases in rat liver. Biochim. Appl. 9, 238 (1962).Google Scholar
  2. Anderson, J. S., M. Matsuhashi, M. A. Haskin, and J. L. Strominger: Lipid-phosphodisaccharide-pentapeptide: A presumed membrane transport intermediate in the biosynthesis of bacterial cell walls. Proc. Natl. Acad. Sci. U.S. 53, 881 (1965).CrossRefGoogle Scholar
  3. Aoki, T.: The mode of action of cycloserine. II. The influence on glutamic-aspartic transamination. Kekkaku 32, 544 (1957); cited from Chem. Abstr. 52, 7427 (1958).PubMedGoogle Scholar
  4. Azarkh, R. M., A. E. Braunstein, T. S. Paskhina, and T. S. Syui: The Effect of the optical isomers of cycloserine on the activity of certain transaminases. Biokhimiya 25, 954 (1960); Biochemistry (U.S.S.R.) 25, 741 (1961).Google Scholar
  5. Barbieri, P., A. DI Marco, I. Fuoco, and A. Rusconi: Investigations on the mode of action of cycloserine upon protein synthesis in Escherichia coli. Biochem. Pharmacol. 3, 101 (1960).PubMedCrossRefGoogle Scholar
  6. Bonavita, V.: Purification and properties of glutamic-oxaloacetic transaminase from human brain. J. Neurochem. 4, 275 (1959).PubMedCrossRefGoogle Scholar
  7. Bondi, A., J. Kornblum, and C. Forte: Inhibition of antibacterial activity of cycloserine by alpha-alanine. Proc. Soc. Exptl. Biol. Med. 96, 270 (1957).Google Scholar
  8. Bottero, A., G. Perna, G. C. Colombi, and F. Leidi: Experimental and clinical studies on cycloserine resistance. Giorn. ital. tuberc. 12, 10 (1958).Google Scholar
  9. Braunstein, A. E.: Studies on the properties, mode of action, and selective inhibition of transaminase, In P. A. E. Desnuelle (Editor), Proceedings of the Fifth Internat. Congr. of Biochemistry, Moscow, 1962, vol. IV, p. 280. New York: Pergamon Press 1963.Google Scholar
  10. Braunstein, A. E., R. M. Azarkh, and T. A. Syui: Kinetics of inhibition of transaminases by cycloserine. Biokhimiya 26, 882 (1961); Biochemistry (U.S.S.R.) 27, 760 (1962).Google Scholar
  11. Brettschneider, H., u. W. Vetter: Synthese des DL-4-Amino-3-isoxazolidons sowie seiner D-Form, des natürlichen Cycloserins. Monatsh. Chem. 90, 799 (1959).CrossRefGoogle Scholar
  12. Brettschneider, H., W.Vetter u. E. Semenitz: Synthese und antibakterielle Eigenschaften des D, L-N, N-Dimethylcycloserins. Monatsh. Chem. 89, 627 (1958).CrossRefGoogle Scholar
  13. Breger, M. A.: The biological activity of cycloserine and some of its analogues and homologues. Antibiotiki 6, 26 (1961).PubMedGoogle Scholar
  14. Buogo, A., A. DI Marco, M. Ghione, A. Migliacci, and A. Sanfilippo: Antagonism of D-and L-alanine of the enantiomorphic forms of cycloserine. Giorn. microbiol. 6, 131 (1958); cited from Chem. Abstr. 54, 17538 (1960).Google Scholar
  15. Chambers, P., J. Bing, J. Lynch, F. C. Neuhaus, and R. W. Brockman: Effects of cycloserine and related compounds on cell wall synthesis in sensitive and resistant Escherichia coli. Bacteriol. Proc. 119 (1963).Google Scholar
  16. Chatterjee, A.N., and J. T. Park: Biosynthesis of cell wall mucopeptide by a particulate fraction from Staphylococcus aureus. Proc. Natl. Acad. Sci. U.S. 51, 9 (1964).CrossRefGoogle Scholar
  17. Ciak, J., and F. E. Hahn: Mechanisms of action of antibiotics. II. Studies on the modes of action of cycloserine and its L-stereoisomer. Antibiotics & Chemotherapy 9, 47 (1959).Google Scholar
  18. Cohen, A. C., and I. C. Dross: 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
  19. Comb, D. G.: The enzymatic addition of D-alanyl-D-alanine to a uridine nucleotidepeptide. J. Biol. Chem. 237, 1601 (1962).PubMedGoogle Scholar
  20. Cuckler, A.C., B.M. Frost, L. McClelland, and M. Solotorovsky: The antimicrobial evaluation of oxamycin (D-4-amino-3-isoxazolidone), a new broadspectrum antibiotic. Antibiotics & Chemotherapy 5, 191 (1955).Google Scholar
  21. Cummings, M. M., R. A. Patnode, and P. C. Hudgins: Effects of cycloserine on Mycobacterium tuberculosis in vitro. Antibiotics & Chemotherapy 5, 198 (1955).Google Scholar
  22. Cummings, 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
  23. Curtiss, R., L. J. Charamella, C. M. Berg, and P. E. Harris: Kinetic and genetic analyses of D-cycloserine inhibition and resistance in Escherichia coli. J. Bacteriol. 90, 1238 (1965).PubMedGoogle Scholar
  24. Dann, O. T., and C. E. Carter: Cycloserine inhibition of gamma-aminobutyric-alpha-ketoglutaric transaminase. Biochem. Pharmacology 13, 677 (1964).CrossRefGoogle Scholar
  25. Davis, B.D., and M.K. Maas: Analysis of the biochemical mechanism of drug resistance in certain bacterial mutants. Proc. Natl. Acad. Sci. U.S. 38, 775 (1952).CrossRefGoogle Scholar
  26. Demerec, M.: Origin of bacterial resistance to antibiotics. J. Bacteriol. 56, 63 (1948).Google Scholar
  27. Dengler, H. J.: Zur Hemmung der L-Glutaminsäure-und L-Dopadecarboxylase durch D-Cycloserin und andere Isoxazolidone. Naunyn-Schmiedeberg’s Arch. Exptl. Pathol. u.Pharmakol. 243, 366 (1962).CrossRefGoogle Scholar
  28. Epstein, I. G., K. G. S. Nair, and L. J. Boyd: 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
  29. Feth, T., and K. Kazim: In vitro action of cycloserine on Mycobacterium tuberculosis. Bacteriol. Proc. 85 (196Google Scholar
  30. Folkers, K.: 4-Pyridoxylamino-3-isoxazolidone compounds. U.S.Patent 2, 776, 296 (January 1, 1957).Google Scholar
  31. Frecking, M. G., and P. D. Hoeprich: Effect of cycloserines on D-amino acid oxidase. Arch. Biochem. Biophys. 115, 108 (1966).PubMedCrossRefGoogle Scholar
  32. Freese, E., and J. Oosterwyk: The induction of alanine dehydrogenase. Biochemistry 2, 1212 (1963).PubMedCrossRefGoogle Scholar
  33. Grosset, J., and G. Canetti: Incidence of resistance to secondary antimicrobials in wild strains of M. tuberculosis (PAS, ethionamide, cycloserine, viomycin, and kanamycin). Ann. Inst. Pasteur 103, 163 (1962).Google Scholar
  34. Grula, M. M., and E. A. Grula: Action of cycloserine on a species of Erwinia with reference to cell division. Can. J. Microbiol. 11, 453 (1965).PubMedCrossRefGoogle Scholar
  35. Grula, E. A., and M. M. Grula: Cell division in a species of Erwinia. VII. Amino sugar content of dividing and nondividing cells. Biochem. Biophys. Research Commun. 17, 341 (1964).CrossRefGoogle Scholar
  36. Hagemann, G., L. Penasse et J. Teillon: Sur un derive de la serine, la O-carbamyl-D-serine produit par un streptomyces. Biochim. et Biophys. Acta 17, 240 (1955).CrossRefGoogle Scholar
  37. Hahn, F. E., and J. Ciak: Penicillin-induced lysis of Escherichia coli. Science 125, 119 (1957).PubMedCrossRefGoogle Scholar
  38. Hancock, R., and P. C. Fitz-James: Some differences in the action of penicillin, bacitracin, and vancomycin on Bacillus megaterium. J. Bacteriol. 87, 1044 (1964).PubMedGoogle Scholar
  39. Harned, R. L., P. H. Hidy, and E. K. La Baw: Cycloserine. I. A preliminary report. Antibiotics & Chemotherapy 5, 204 (1955).Google Scholar
  40. Harris, D. A., M. Ruger, M. A. Reagan, F. J. Wolf, R. L. Peck, H. Wallick, and H. B. Woodruff: Discovery, development, and antimicrobial properties of D-4-amino-3-isoxazolidone (oxamycin), a new antibiotic produced by Streptomyces garyphalus n. sp. Antibiotics & Chemotherapy 5, 183 (1955).Google Scholar
  41. Harris, D. A., F. J. Wolf, and R. L. Peck: Crystalline alkaline earth metal salts of 4-amino-3-isoxazolidone. U.S. Patent 2, 832, 788 (April 29, 1958).Google Scholar
  42. Hayashi, K., C. G. Skinner, and W. Shive: Synthesis and biological properties of 4-amino-5-isopropyl-3-isoxazolidone, a substituted cycloserine. J. Org. Chem. 26, 1167 (1961).CrossRefGoogle Scholar
  43. Hidy, P. H., E. B. Hodge, V. V. Young, R. L. Harned, G. A. Brewer, W. F. Phillips, W. F. Runge, H. E. Staveley, A. Pohland, H. Boaz, and H. R. Sullivan: Structures and reactions of cycloserine. J. Am. Chem. Soc. 77, 2345 (1955)CrossRefGoogle Scholar
  44. Hodge, E. B.: Substituted cycloserines. U.S. Patent 2, 971, 004 (February 7, 1961 a).Google Scholar
  45. Hodge, E. B.: N-(p-Chlorobenzyl)-cycloserine. U.S. Patent 2, 967, 866 (January 10, 1961b).Google Scholar
  46. Hoeprich, P.D.: Alanine: Cycloserine antagonism. III. Quantitative aspects and relations to heating of culture media. J. Lab. Clin. Med. 62, 657 (1963).PubMedGoogle Scholar
  47. Hoeprich, P. D.: Alanine: Cycloserine antagonism. VI. Demonstration of D-alanine in the serum of guinea pigs and mice. J. Biol. Chem. 240, 1654 (1965)PubMedGoogle Scholar
  48. Holly, F. W., Cranford, and C. H. Stammer: Synthesis of 4-amino-3-isoxazolidone and its derivatives. U.S. Patent 2, 772, 281 (November 27, 1956).Google Scholar
  49. Howe, W. B., G. L. Melson, C. H. Meredith, J. R. Morrison, M. H. Platt, and J. L. Strominger: Stepwise development of resistance to D-cycloserine in Staphylococcus aureus. J. Pharmacol. Exptl. Therap. 143, 282 (1964).Google Scholar
  50. Ikawa, M., and E. E. Snell: Cell wall composition of lactic acid bacteria. J. Biol. Chem. 235, 1376 (1960).PubMedGoogle Scholar
  51. Ishii, K., and M. G. Sevag: Inhibition by cycloserine of the synthesis of 5-amino-4-imidazolecarboxamide by Escherichia coli. Antibiotics & Chemotherapy 6, 500 (1956).Google Scholar
  52. Ito, E., and M. Saito: Time course of accumulation of UDP-N-acetylamino sugar derivatives in Staphylococcus aureus. Biochim. et Biophys. Acta 78, 237 (1963).CrossRefGoogle Scholar
  53. Ito, E., and J. L. Strominger: Enzymatic synthesis of the peptide in bacterial uridine nucleotides. I. Enzymatic addition of L-alanine, D-glutamic acid, and L-lysine. J. Biol. Chem. 237, 2689 (1962a).Google Scholar
  54. Ito, E., and J. L. Strominger: Enzymatic synthesis of the peptide in bacterial uridine nucleotides. II. Enzymatic synthesis and addition of D-alanyl-D-alanine. J. Biol. Chem. 237, 2696 (1962b).Google Scholar
  55. Ito, F., T. Aoki, M. Yamamoto, M. Yuasa, H. Mizobata, and K. Tone: The mode of action of cycloserine (CS). Med. J. Osaka Univ. 9, 23 (1958).Google Scholar
  56. Karpeiskii, M. Ya., R. M. Khomutov, E. S. Severin, and Yu. N. Breusov: The investigation of the interaction of cycloserine and related compounds with aspartate-glutamate transaminase. In: E. E. Snell, P. M. Fasella, A. E. Braunstein, and A. Rossi-Fanelli (editors), Chemical and Biological Aspects of Pyridoxal Catalysis. I.U.B. Symposium Series, vol. 30, p. 323. New York: Pergamon Press 1963a.Google Scholar
  57. Karpeiskii, M. Ya., Yu. N. Breusov, R. M. Khomutov, E. S. Severin, and O. L. Polyanovskii: The mechanism of reaction of cycloserine and related compounds with aspartate-glutamate transaminase. Biokhimiya 28, 345 (1963b); Biochemistry (U.S.S.R.) 28, 280 (1964).Google Scholar
  58. Karpeiskii, M. Ya., and Yu. N. Breusov: On the structure of the enzyme-inhibitor complex of aspartate-transaminase with L-cycloserine. Biokhimiya 30, 153 (1965).Google Scholar
  59. Khomutov, R. M., M. Ya. Karpeiskii, E. S. Severin, E. I. Budovskii, and N. K. Kochetkov: Cycloserine and related compounds. VI. Synthesis of analogs of cycloserine with a substitued amino group. J. gen. Chem. (U.S.S.R.) 29, 636 (1959).Google Scholar
  60. Khomutov, R. M., M. Ya. Karpeiskii, C. Chi-Pin, and N. K. Kochetkov: Cycloserine and related compounds. XL. 4-Hydroxy-3-isoxazolidinone and some of its derivatives. Zhur. Obshchei Khim. 30, 3057 (1960); J. Gen. Chem. (U.S.S.R.) 30, 3030 (1961).Google Scholar
  61. Khomutov, R. M., M. Ya. Karpeiskii, and E. S. Severin: The relationship between biological activity and chemical properties. Biokhimiya 26, 772 (1961); Biochemistry (U.S.S.R.) 26, 667 (1962).Google Scholar
  62. Khomutov, R. M., M. Ya. Karpeiskii, M. A. Breger, and E. S. Severin: On some cycloserine derivatives possessing antitubercular activity. Voprosy Med. Khim. 8, 389 (1962).Google Scholar
  63. Khomutov, R. M., M. Ya. Karpeiskii, and E. S. Severin: The predetermined synthesis of inhibitors for pyridoxalic enzymes. In: E. E. Snell, P. M. Fasella, A. E. Braunstein, and A. Rossi-Fanelli (editors), Chemical and Biological Aspects of Pyridoxal Catalysis. I.U.B. Symposium Series, vol. 30, p. 323. New York: Pergamon Press 1963Google Scholar
  64. Kihara, H., M. Ikawa, and E. E. Snell: Peptides and bacterial growth. X. Relation of uptake and hydrolysis to utilization of D-alanine peptides for growth of Streptococcus faecalis. J. Biol. Chem. 236, 172 (1961).PubMedGoogle Scholar
  65. Kochetkov, N. K., R. M. Khomutov, and M. Ya. Karpeiskii: New synthesis of cycloserine. Dokl. Akad. Nauk S.S.S.R. 111, 831 (1956).Google Scholar
  66. Kochetkov, N. K., E. I. Budovskii, R. M. Khomutov, and M. Ya. Karpeiskii: Cycloserine and related compounds. V. Cyclization of alpha-benzoylamino-beta-arylacrylohydroxamic acids. J. Gen. Chem. (U.S.S.R.) 29, 630 (1959).Google Scholar
  67. Kolesinska, J.: Cycloserine stability at various temperatures and pH values. Med. Doswiadczalna i. Mikrobiol. 13, 189 (1961); cited from Chem. Abstr. 55, 24883 (1961).Google Scholar
  68. Kotschetkow, N. K.: Die Chemie des Antibiotikums Cykloserin. Österr. Chemiker-Ztg. 62, 276 (1961).Google Scholar
  69. Kuehl, F. A., F. J. Wolf, N. R. Trenner, R. L. Peck, E. Howe, B. D. Hunnewell, G. Downing, E. Newstead, R. P. Buhs, I. Putter, R. Ormond, J. E. Lyons, L. Chalet, and K. Folkers: D-4-Amino-3-isoxazolidone, a new antibiotic. J. Am. Chem. Soc. 77, 2344 (1955).CrossRefGoogle Scholar
  70. Kurihara, T., and K. Chiba: Orientomycin, a new antibiotic. Ann. Rept. Tohoku coll. Pharm. 3, 83 (1956); cited from Chem. Abstr. 51, 5197 (1957).Google Scholar
  71. Lark, C., and R. Schichtel: Comparison of spheroplast induction in Alcaligenes faecalis by three different agents. J. Bacteriol. 84, 1241 (1962).PubMedGoogle Scholar
  72. Lester, W., A. Salomin, A. F. Reimann, E. Shulruff, and G. S. Gerg: Cycloserine therapy in tuberculosis in humans. Am. Rev. Tuberc. 74, 121 (1956).PubMedGoogle Scholar
  73. Lillick, L., R. Strang, L. J. Boyd, M. Schwimmer, and M. G. Mulinos: Cycloserine in the treatment of nontuberculosis infections. Antibiotics Ann. 1955/56, 158.Google Scholar
  74. Longenecker, J. B., and E. E. Snell: Pyridoxal and metal ion catalysis of alpha-beta-elimination reactions of serine-3-phosphate and related compounds. J. Biol. Chem. 225, 409 (1957).PubMedGoogle Scholar
  75. Lynch, J. L., and F. C. Neuhaus: On the mechanism of action of the antibiotic O-carbamyl-D-serine in Streptococcus faecalis R. J. Bacteriol. 91, 449 (1966).PubMedGoogle Scholar
  76. Malamy, M. H., and B. L. Horecker: Release of alkaline phosphates from cells of Escherichia coli upon lysozyme spheroplast formation. Biochemistry 3, 1889 (1964).PubMedCrossRefGoogle Scholar
  77. Martinez-Carrion, M., and W. T. Jenkins: D-Alanine-D-glutamic transaminase. II. Inhibitors and the mechanism of transamination of D-amino acids. J. Biol. Chem. 240, 3547 (1965).PubMedGoogle Scholar
  78. Meadow, P. M., J. S. Anderson, and J. L. Strominger: Enzymatic polymerization of UDP-acetylmuramyl-L-ala-D-glu-L-lys-D-ala-D-ala and UDP-acetylglucosamine by a particulate enzyme from Staphylococcus aureus and its inhibition by antibiotics. Biochem. Biophys. Research Commun. 14, 382 (1964).CrossRefGoogle Scholar
  79. Michalský, J., J. Opíhal u. J. Čtvrtnik: Cycloserin und verwandte Verbindungen; Über die Kondensationsprodukte von D, L-4-Amino-3-isoxazolidon und 2, 5-Bis (aminooxymethyl)-3, 6-diketopiperazin. Monatsh. Chem. 93, 618 (1962a).CrossRefGoogle Scholar
  80. Michalský, J., J. Čtvrtnik, Z. Horáková u. V. Bydžovský: Über die tuberkulostatische Aktivität von 2, 5-Bis-(aminoxymethyl)-3, 6-diketopiperazin, eines Umwandlungsproduktes des Cyclo serins Experientia. 18, 217 (1962b).PubMedCrossRefGoogle Scholar
  81. Michel, M. F., and W. Hijmans: 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. 23, 35 (1960).Google Scholar
  82. Mora, J., and L. F. Bojalil: Antagonism of the D-alanine reversal of D-cycloserine action by L-alanine in Mycobacterium acapulcensis. Proc. Soc. Exptl. Biol. Med. 119, 49 (1965).Google Scholar
  83. Mora, J., and E. E. Snell: The uptake of amino acids by cells and protoplasts of Streptococcus faecalis. Biochemistry 2, 136 (1963).CrossRefGoogle Scholar
  84. Morrison, N. E.: The reversal of D-cycloserine inhibition of mycobacterial growth. Bacteriol. Proc. 86 (1962).Google Scholar
  85. Moulder, J. W., D. L. Novosel, and J. E. Officer: Inhibition of the growth of agents of the psittacosis group by D-cycloserine and its specific reversal by D-alanine. J. Bacteriol. 85, 707 (1963).PubMedGoogle Scholar
  86. Moulder, J. W., D. L. Novosel, and I. I. E. Tribby: Changes in mouse pneumonitis agent associated with development of resistance to Chlortetracycline. J. Bacteriol. 89, 17 (1965).PubMedGoogle Scholar
  87. Moyed, H. S.: Biochemical mechanisms of drug resistance. Ann. Rev. Microbiol. 18, 247 (1964).CrossRefGoogle Scholar
  88. Mulinos, M. G.: Cycloserine: An antibiotic paradox. Antibiotics Ann. 1955/56, 131.Google Scholar
  89. Murari, G., G. Salgarello, and R. Moratello: Antibacterial activity of optical isomers of cycloserine and of its synthetic intermediate (isoxazolidone). Action on Escherichia coli and Salmonella. Boll. soc. ital. biol. sper. 34, 1534 (1958); cited from Chem. Abstr. 55, 14583 (1961).PubMedGoogle Scholar
  90. Nakamura, M.: Amebacidal action of cycloserine. Experientia 13, 29 (1957).CrossRefGoogle Scholar
  91. Neilands, J. B.: Metal and hydrogen-ion binding properties of cycloserine. Arch. Biochem. Biophys. 62, 151 (1956).PubMedCrossRefGoogle Scholar
  92. Neuhaus, F. C., and W. G. Struve: Enzymatic synthesis of analogs of the cell-wall precursor. I. Kinetics and specificity of uridine diphospho-N-acetyl-muramyl-L-alanyl-D-glutamyl-L-lysine: D-Alanyl-D-alanine ligase (adenosine diphosphate) from Streptococcus faecalis R. Biochemistry 4, 120 (1965).PubMedCrossRefGoogle Scholar
  93. Neuhaus, F. C.: The enzymatic synthesis of D-alanyl-D-alanine. I. Purification and properties of D-alanyl-D-alanine synthetase. J. Biol. Chem. 237, 778 (1962a).PubMedGoogle Scholar
  94. Neuhaus, F. C.: The enzymatic synthesis of D-alanyl-D-alanine. II. Kinetic studies of D-alanyl-D-alanine synthetase. J. Biol. Chem. 237, 3128 (1962b).PubMedGoogle Scholar
  95. Neuhaus, F. C., and J. L. Lynch: The enzymatic synthesis of D-alanyl-D-alanine. III. On the inhibition of D-alanyl-D-alanine synthetase by the antibiotic D-cycloserine. Biochemistry 3, 471 (1964).PubMedCrossRefGoogle Scholar
  96. Nitti, V., and M. Tsukamura: Resistance of tuberculosis mycobacteria to cycloserine in vitro. Arch. tisiol. mal. app. respirat. (Naples) 12, 71 (1957); cited from Chem. Abstr. 51, 13069 (1957).Google Scholar
  97. Okami, Y., K. Maeda, H. Kondo, T. Tanaka, and H. Umezawa: A streptomyces producing O-carbamyl-D-serine. J. Antibiotics (Japan), Ser. A 15, 147 (1962).Google Scholar
  98. Park, J. T.: Selective inhibition of bacterial cell-wall synthesis: Its possible applications in chemotherapy. Symp. Soc. Gen. Microbiol. 8, 49 (1958a).Google Scholar
  99. Park, J. T.: Inhibition of cell-wall synthesis in Staphylococcus aureus by chemicals which cause accumulation of wall precursors. Biochem. J. 70, 2 P (1958b).Google Scholar
  100. Park, 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
  101. Park, J. T., and R. Hancock: A fractionation procedure for studies of the synthesis of cell-wall mucopeptide and of other polymers in cells of Staphylococcus aureus. J. Gen. Microbiol. 22, 249 (1960).PubMedGoogle Scholar
  102. Paskhina, T. S.: Effect of isomers of cycloserine on the activity of D-alanine-D-glutamic transaminase of Bacillus subtilis. Voprosy Med. Khim. 10, 526 (1964); cited from Chem. Abstr. 57, 2978 (1965).Google Scholar
  103. Patnode, R. A., P. C. Hudgins, and M. M. Cummings: Effect of cycloserine on experimental tuberculosis in guinea pigs. Am. Rev. Tuberc. Pulmonary Diseases 72, 117 (1955).Google Scholar
  104. Pepinsky, R.: X-Rays and the absolute configuration of optically active molecules. Record Chem. Progr. 17, 145 (1956).Google Scholar
  105. Perry, D., and H. D. Slade: Intraspecific and interspecific tranformation in Streptococci. J. Bacteriol. 88, 595 (1964).PubMedGoogle Scholar
  106. Pietra, G. D., F. DeLorenzo, and G. Illiano: Biochim. Appl. 10, 123 (1963); cited from F. Cedrangolo, in E. E. Snell, P. M. Fasella, A. E. Braunstein, and A. Rossi-Fanelli (editors), Chemical and Biological Aspects of Pyridoxal Catalysis, p. 343. New York: Pergamon Press 1Google Scholar
  107. Pittillo, R. F., and J. W. Foster: Potentiation of Inhibitor action through determination of reversing metabolites. J. Bacteriol. 67, 53 (1953)Google Scholar
  108. Plapp, R., U. O. Kandler: Zur Wirkung zellwandhemmender Antibiotica bei gramnegativen Bakterien. II. Die Wirkung von D-Cycloserin auf die Konzentration von Zellwandvorstufen in Proteus mirabilis und dessen L-Phase. Arch. Mikrobiol. 50, 282 (1965).PubMedCrossRefGoogle Scholar
  109. Pohland, A.: 3-Isoxazolidones, derivatives and process. U.S. Patent 2, 762, 815 (September 11, 1956).Google Scholar
  110. Polyanovskii, O. L., and Y. M. Torchinskii: 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. 141, 488 (1961).Google Scholar
  111. Plattner, Pl. A., A. Boller, H. Frick, A. Fürst, B. Hegedüs, H. Kirchensteiner, St. Majnoni, R. Schläpfer u. H. Spiegelberg: Synthesen des 4-Amino-3-isoxazolidinons (Cycloserin) und einiger Analoga. Helv. Chim. Acta 40, 1531 (1957)CrossRefGoogle Scholar
  112. Ratouis, R., and R. Behar: Synthesis of 4-amino-3-isoxazolidinone. Bull. soc. chim. France 1957, 1255Google Scholar
  113. Reitz, R., H. D. Slade, and F. C. Neuhaus: On the biochemical basis of D-cycloserine resistance. Federation Proc. Abstracts 25, 344 (1966).Google Scholar
  114. Robson, J. M., and F.M.Sullivan: Antituberculosis drugs. Pharmacol. Rev. 15, 195 (1963).Google Scholar
  115. Rogers, H. J., and A. J. Garrett: The interrelationship between mucopeptide and ribitol teichoic acid formation as shown by the effect of inhibitors. Biochem. J. 96, 231 (1965).PubMedGoogle Scholar
  116. Roze, 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
  117. Roze, U., and J. L. Strominger: The non-enzymatic reaction between D-cycloserine and pyridoxal phosphate. Federation Proc. Abstracts 22, 423 (1963).Google Scholar
  118. Roze, U., and J. L. Strominger: Alanine racemase from Staphylococcus aureus: Conformation of its substrates and its inhibitor; D-cycloserine. J. Mol. Pharmacol. 2, 92 (1966).Google Scholar
  119. Runge, W. F.: Process of producing acetyl cycloserine. U.S. Patent 2, 815, 348 (December 3, 1957).Google Scholar
  120. Russell, W. F. Jr., and G. Middlebrook: Chemotherapy of tuberculosis. Springfield (I11.): Ch. C. Thomas 1961.Google Scholar
  121. Saito, M., N. Ishimoto, and E. Ito: Uridine diphosphate N-acetylamino sugar derivatives in penicillin-treated Staphylococcus aureus. J. Biochemistry (Tokyo) 54, 273 (1963).Google Scholar
  122. Salgarello, G., and E. Turri: Antibacterial activity of optical isomers of cycloserine. Action on Mycobacterium tuberculosis. Boll. soc. ital. biol. sper. 34, 1538 (1958); cited from Chem. Abstr. 55, 14583 (1961).PubMedGoogle Scholar
  123. Salton, M. R. J.: The anatomy of the bacterial surface. Bacteriol. Rev. 25, 77 (1961).PubMedGoogle Scholar
  124. Salton, M. R. J.: The Bacterial Cell Wall, p. 107. Amsterdam: Elsevier Publ. Co. 1964.Google Scholar
  125. Saukkonen, J., and P. Virkola: Acid-soluble nucleotides of Staphylococcus aureus. Ann. Med. Exptl. et Biol. Fenniae (Helsinki) 41, 220 (1963).Google Scholar
  126. Serembe, M.: Antituberculous action of levorotatory and dextrorotatory cycloserine and of some synthetic intermediates. Minerva med. 1957, 3548; cited from Chem. Abstr. 52, 18837 (1958).Google Scholar
  127. Shockman, G. D.: Reversal of cycloserine inhibition by D-alanine. Proc. Soc. Exptl. Biol. Med. 101, 693 (1959).Google Scholar
  128. Shockman, G. D., and J.O. Lampen: Inhibition by antibiotics of the growth of bacterial and yeast protoplasts. J. Bacteriol. 84, 508 (1962).PubMedGoogle Scholar
  129. Shull, G. M., and J. L. Sardinas: PA-94, an antibiotic identical with D-4-amino-3-isoxazolidinone (cycloserine, oxamycin). Antibiotics & Chemotherapy 5, 398 (1955).Google Scholar
  130. Shull, G. M., J. B. Routien, and A. C. Finlay: Cycloserine and production there of. U.S. Patent 2, 773, 878 (December 11, 1956).Google Scholar
  131. Skinner, C. G., T. J. McCord, J.M. Ravel, and W. Shive: O-Carbamyl-L-serine, an inhibitory analog of L-glutamine. J. Am. Chem. Soc. 78, 2412 (1955).CrossRefGoogle Scholar
  132. Smith, J. L., and E. D. Weinberg: Mechanisms of antibacterial action of bacitracin. J. Gen. Microbiol. 28, 559 (1962).PubMedGoogle Scholar
  133. Smrt, J., J. Beranek, J. Sicher, and F. Sorm: Synthesa 4-amino-3-isoxazolidinonu (cykloserinu). Chem. listy 51, 112 (1957a).Google Scholar
  134. Smrt, J., J. Beranek, J. Sicher, J. Skoda, V. F. Hess, and F. Sorm: Synthesis of L-4-amino-3-isoxazolidinone, the unnatural stereoisomer of cycloserine and its antibiotic activity. Experientia 13, 291 (1957b).PubMedCrossRefGoogle Scholar
  135. Snow, G. A.: Structure of mycobactin. Biochem. J. 97, 166 (1965).PubMedGoogle Scholar
  136. Stammer, C. H.: Beta-Aminoxy-D-alanine. J. Org. Chem. 27, 2957 (1962).CrossRefGoogle Scholar
  137. Stammer, C. H., and J. D. McKinney: Cycloserine. III. A schiff base and its reactions. J. Org. Chem. 30, 3436 (1965).PubMedCrossRefGoogle Scholar
  138. Stammer, C. H., A. N. Wilson, C. F. Spencer, F. W. Bachelor, F. W. Holly, and K. Folkers: Synthesis of D-4-amino-3-isoxazolidone. J. Am. Chem. Soc. 79, 3236 (1957).CrossRefGoogle Scholar
  139. Stammer, C. H., A.N. Wilson, F. W. Holly, and K. Folkers: Synthesis of D-4-amino-3-isoxazolidone. J. Am. Chem. Soc. 77, 2346 (1955).CrossRefGoogle Scholar
  140. Steenken, W. Jr, and E. Wolinsky: Cycloserine: Antituberculous activity in vitro and in the experimental animal. Am. Rev. Tuberc. Pulmonary Diseases 73, 539 (1956).Google Scholar
  141. Strominger, J. L.: Biosynthesis of bacterial cell walls. Federation Proc. 21, 134 (1962).Google Scholar
  142. Strominger, J. L., R. H. Threnn, and S.S. Scott: Oxamycin, a competitive antagonist of the incorporation of D-alanine into a uridine nucleotide in Staphylococcus aureus. J. Am. Chem. Soc. 81, 3803 (1959).CrossRefGoogle Scholar
  143. Strominger, J. L., E. Ito, and R. H. Threnn: Competitive inhibition of enzymatic reactions by oxamycin. J. Am. Chem. Soc. 82, 998 (1960).CrossRefGoogle Scholar
  144. Strominger, J. L., J. T. Park, and R. E. Thompson: Composition of the cell wall of Staphylococcus aureus: Its relation to the mechanism of action of penicillin. J.Biol. Chem. 234, 3263 (1959).PubMedGoogle Scholar
  145. Struve, W. G., and F. C. Neuhaus: Evidence for an initial acceptor of UDP-NAc-muramyl-pentapeptide in the synthesis of bacterial mucopeptide. Biochem. Biophys. Research Commun. 18, 6 (1965).CrossRefGoogle Scholar
  146. Struve, W. G., R. K. Sinha, and F. C. Neuhaus: On the initial stage in peptidoglycan synthesis. Phospho-N-acetyl-muramyl-pentapeptide translocase (uridine monophosphate). Biochemistry 5, 82 (1966).PubMedCrossRefGoogle Scholar
  147. Sutton, W. B., and L. Stanfield: The reversal of cycloserine inhibition by mycobactin, a growth factor for mycobacteria. Antibiotics & Chemotherapy 5, 582 (1955).Google Scholar
  148. Tanaka, N.: Mechanism of action of O-carbamyl-D-serine, a new member of cell wall synthesis inhibitors. Biochem. Biophys. Research Commun. 12, 68 (1963).CrossRefGoogle Scholar
  149. Tanaka, N., and K. Sashikata: Biogenesis of D-4-amino-3-isoxazolidone and O-carbamyl-D-serine. J. Gen Appl. Microbiol. 9, 409 (1963).CrossRefGoogle Scholar
  150. Tanaka, N., K. Sashikata, T. Wada, S. Sugawara, and H. Umezawa: Mechanism of action of O-carbamyl-D-serine. J. Antibiotics, Ser. A 16, 217 (1963).Google Scholar
  151. Tanaka, N., and H. Umezawa: Synergism of D-4-amino-3-isoxazolidone and O-carbamyl-D-serine. J. Antibiotics, Ser. A 17, 8 (1964).Google Scholar
  152. Toennies, G., and G. D. Shockman: Growth chemistry of Streptococcus faecalis. Proceedings of the fourth internat. Congr. of Biochemistry, vol. 13, p. 365. London: Pergamon Press 1959.Google Scholar
  153. Trivellato, E.: Stereoisomers of cycloserine. II. Activity against Escherichia coli in synthetic media. Arch. intern, pharmacodynamie 117, 317 (1958).Google Scholar
  154. Trivellato, E., and C. Concilio: Stereoisomers of cycloserine. I. Bacteriostatic activity towards some microorganisms. Arch. intern, pharmacodynamie 117, 313 (1958); cited from Chem. Abstr. 53, 12392 (1959).Google Scholar
  155. Viallier, J., and R. M. Cayré: Bacilles tuberculeus résistants à la cyclosérine. Compt. rend. soc. biol. 152, 776 (1958).Google Scholar
  156. Vyshepan, E. D., K.I. Ivanova, and A. M. Chernukh: Inhibition of glutamicpyruvic transaminase. Byull. Eksptl. Biol. Med. 52, 76 (1961).Google Scholar
  157. Vyshepan, E. D., K.I. Ivanova, and A. M. Chernukh: The effect of D,L-cycloserine on the process of transamination. Byull. Eksptl. Biol. Med. 47, 52 (1959).Google Scholar
  158. Weinberg, E. D.: The mutual effects of antimicrobial compounds and metallic cations. Bacteriol. Rev. 21, 46 (1957).PubMedGoogle Scholar
  159. Wishnow, R. M., J. L. Strominger, C. H. Birge, and R. H. Threnn: Biochemical effects of novobiocin on Staphylococcus aureus. J. Bacteriol. 89, 1117 (1965).PubMedGoogle Scholar
  160. Wood, W. A., and I. C. Gunsalus: D-Alanine formation: A racemase in Streptococcus faecalis. J. Biol. Chem. 190, 403 (1951).PubMedGoogle Scholar
  161. Yamada, K., S. Sawaki, and S. Hayami: Inhibitory effect of cycloserine on some enzymic activities related to vitamin B6. J. Vitaminol. (Osaka) 3, 68 (1957).CrossRefGoogle Scholar
  162. Youmans, G. P., and A. S. Youmans: Experimental chemotherapy of tuberculosis and other mycobacterial infections. In: R. J. Schnitzer and F. Hawking (editors), Experimental Chemotherapy, vol. II, p. 393. New York: Academic Press 1964.Google Scholar
  163. Zygmunt, W. A.: Reversal of D-cycloserine inhibition of bacterial growth by alanine. J. Bacteriol. 84, 154 (1962).PubMedGoogle Scholar
  164. Zygmunt, W. A.: Antagonism of D-cycloserine inhibition of mycobacterial growth by D-alanine. J. Bacteriol. 85, 1217 (1963).PubMedGoogle Scholar

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© Springer-Verlag Berlin · Heidelberg 1967

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  • Francis C. Neuhaus

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