The Fate of Molecular Oxygen in Azinomycin Biosynthesis Academic Article

abstract

• The azinomycins are a family of aziridine-containing antitumor antibiotics and represent a treasure trove of biosynthetic reactions. The formation of the azabicyclo[3.1.0]hexane ring and functionalization of this ring system remain the least understood aspects of the pathway. This study reports the incorporation of 18O-labeled molecular oxygen in azinomycin biosynthesis including both oxygens of the diol that ultimately adorn the aziridino[1,2- a]pyrrolidine moiety. Likewise, two other sites of heavy atom incorporation are observed.

authors

• Watanabe, Coran

altmetric score

• 0.75

author list (cited authors)

• Kelly, G. T., Washburn, L. A., & Watanabe, C.

citation count

• 6

complete list of authors

• Kelly, Gilbert T||Washburn, Lauren A||Watanabe, Coran MH

publication date

• January 2019

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of Organic Chemistry  Journal

keywords

• Azabicyclo Compounds
• Chromatography, Thin Layer
• Dipeptides
• Intercellular Signaling Peptides And Proteins
• Naphthalenes
• Oxygen
• Streptomyces

Digital Object Identifier (DOI)

• 10.1021/acs.joc.8b03007

start page

• 2991

end page

• 2996

volume

• 84

issue

• 5

URL

• http://dx.doi.org/10.1021/acs.joc.8b03007