Exploration of the molecular origin of the azinomycin epoxide: timing of the biosynthesis revealed.
Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.
Department of Chemistry, Texas A&M University, College Station, Texas 77842, USA.
Vasudha
V
Sharma
Gilbert T
GT
Kelly
Coran M H
CM
Watanabe
D053961:Azabicyclo Compounds; D004151:Dipeptides; D004852:Epoxy Compounds / Q000737:chemistry* / Q000378:metabolism*; D006020:Glycopeptides / Q000737:chemistry; D036341:Intercellular Signaling Peptides and Proteins; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism*; D010455:Peptides / Q000737:chemistry; D013997:Time Factors
D053961:Azabicyclo Compounds; D004151:Dipeptides; D004852:Epoxy Compounds; D006020:Glycopeptides; D036341:Intercellular Signaling Peptides and Proteins; D009281:Naphthalenes; D010455:Peptides; C515726:azinomycin epoxide; C051055:azinomycin B; C051054:azinomycin A