L [αS, 5S] α amino 3 chloro 4,5 dihydro 5 isoxazoleacetic acid (NSC 163501)

a new amino acid antibiotic with the properties of an antagonist of L glutamine

H. N. Jayaram, D. A. Cooney, J. A. Ryan

Research output: Chapter in Book/Report/Conference proceedingChapter

94 Citations (Scopus)

Abstract

L [αS,5S] α amino 3 chloro 4,5 dihydro 5 isoxazoleacetic acid (NSC 163501), an antibiotic elaborated by Streptomyces sviceus, has been shown to be a powerful inhibitor of many mammalian and bacterial reactions involving the transfer of nitrogen from the γ carboxamide of L glutamine. Thus, the utilization of L glutamine for the synthesis of carbamyl phosphate, L asparagine, guanosine 5' monophosphate, cytidine 5' triphosphate, N formylglycinamidine ribonucleotide, NAD, glucosamine 6 phosphate, and anthranilic acid is strongly or totally inhibited by a concentration of NSC 163501 of 1 x 10-3 M. L Glutamate synthetase of Escherichia coli is only modestly inhibited and 5 phosphoribosylamine synthesis in fetal rat liver is comparatively refractory to inhibition. NSC 163501 treatment of L1210 cells growing in a low L glutamine culture medium produced arrest in G1 or early S phase. Of the amino acids tested, only L glutamine antagonized such growth inhibition.

Original languageEnglish (US)
Title of host publicationCANCER CHEMOTHER.REP.
Pages481-491
Number of pages11
Volume59
Edition3
StatePublished - 1975
Externally publishedYes

Fingerprint

acivicin
Glutamine
Anti-Bacterial Agents
Amino Acids
Acids
Glutamate Synthase (NADH)
Carbamyl Phosphate
Guanosine Monophosphate
Ribonucleotides
Cytidine Triphosphate
Asparagine
Streptomyces
S Phase
NAD
Culture Media
Nitrogen
Escherichia coli
Liver
Growth

ASJC Scopus subject areas

  • Medicine(all)

Cite this

Jayaram, H. N., Cooney, D. A., & Ryan, J. A. (1975). L [αS, 5S] α amino 3 chloro 4,5 dihydro 5 isoxazoleacetic acid (NSC 163501): a new amino acid antibiotic with the properties of an antagonist of L glutamine. In CANCER CHEMOTHER.REP. (3 ed., Vol. 59, pp. 481-491)

L [αS, 5S] α amino 3 chloro 4,5 dihydro 5 isoxazoleacetic acid (NSC 163501) : a new amino acid antibiotic with the properties of an antagonist of L glutamine. / Jayaram, H. N.; Cooney, D. A.; Ryan, J. A.

CANCER CHEMOTHER.REP.. Vol. 59 3. ed. 1975. p. 481-491.

Research output: Chapter in Book/Report/Conference proceedingChapter

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abstract = "L [αS,5S] α amino 3 chloro 4,5 dihydro 5 isoxazoleacetic acid (NSC 163501), an antibiotic elaborated by Streptomyces sviceus, has been shown to be a powerful inhibitor of many mammalian and bacterial reactions involving the transfer of nitrogen from the γ carboxamide of L glutamine. Thus, the utilization of L glutamine for the synthesis of carbamyl phosphate, L asparagine, guanosine 5' monophosphate, cytidine 5' triphosphate, N formylglycinamidine ribonucleotide, NAD, glucosamine 6 phosphate, and anthranilic acid is strongly or totally inhibited by a concentration of NSC 163501 of 1 x 10-3 M. L Glutamate synthetase of Escherichia coli is only modestly inhibited and 5 phosphoribosylamine synthesis in fetal rat liver is comparatively refractory to inhibition. NSC 163501 treatment of L1210 cells growing in a low L glutamine culture medium produced arrest in G1 or early S phase. Of the amino acids tested, only L glutamine antagonized such growth inhibition.",
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