Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic sibiromycin by streptosporangium sibiricum

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Abstract

The biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum requires the construction of four units: the amino sugar from glucose; the anthranilate ring from DL-tryptophan probably via kynurenine; the aromatic methyl group from methionine; the propylidene proline from L-tyrosine with the loss of two aromatic carbons and addition of a C-1 from methionine. Retention of tritium from DL-[5-3H]tryptophan in sibiromycin suggests an NIH shift during hydroxylation of an intermediate.

Original languageEnglish (US)
Pages (from-to)4225-4229
Number of pages5
JournalBiochemistry
Volume18
Issue number19
StatePublished - 1979
Externally publishedYes

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Biosynthesis
Tryptophan
Methionine
Anti-Bacterial Agents
Amino Sugars
Kynurenine
Hydroxylation
Tritium
Proline
Tyrosine
Carbon
Glucose
Bz-423
sibiromycin
anthranilic acid
methionine methyl ester

ASJC Scopus subject areas

  • Biochemistry

Cite this

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title = "Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic sibiromycin by streptosporangium sibiricum",
abstract = "The biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum requires the construction of four units: the amino sugar from glucose; the anthranilate ring from DL-tryptophan probably via kynurenine; the aromatic methyl group from methionine; the propylidene proline from L-tyrosine with the loss of two aromatic carbons and addition of a C-1 from methionine. Retention of tritium from DL-[5-3H]tryptophan in sibiromycin suggests an NIH shift during hydroxylation of an intermediate.",
author = "Laurence Hurley",
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journal = "Biochemistry",
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AB - The biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum requires the construction of four units: the amino sugar from glucose; the anthranilate ring from DL-tryptophan probably via kynurenine; the aromatic methyl group from methionine; the propylidene proline from L-tyrosine with the loss of two aromatic carbons and addition of a C-1 from methionine. Retention of tritium from DL-[5-3H]tryptophan in sibiromycin suggests an NIH shift during hydroxylation of an intermediate.

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