Exploration of the molecular origin of the azinomycin epoxide: timing of the biosynthesis revealed.

abstract

• 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.

authors

• Watanabe, Coran

altmetric score

• 9

author list (cited authors)

• Sharma, V., Kelly, G. T., & Watanabe, C

citation count

• 27

complete list of authors

• Sharma, Vasudha||Kelly, Gilbert T||Watanabe, Coran MH

publication date

• January 2008

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Azabicyclo Compounds
• Dipeptides
• Epoxy Compounds
• Glycopeptides
• Intercellular Signaling Peptides And Proteins
• Molecular Structure
• Naphthalenes
• Peptides
• Time Factors

PubMed Central ID

• 18841989

Digital Object Identifier (DOI)

• 10.1021/ol8018852

start page

• 4815

end page

• 4818

volume

• 10

issue

• 21

URL

• http%3A%2F%2Fdx.doi.org%2F10.1021%2Fol8018852