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Priming of Azabicycle Biosynthesis in the Azinomycin Class of Antitumor Agents.

Mori, Shogo; Nepal, Keshav K; Kelly, Gilbert T; Sharma, Vasudha; Simkhada, Dinesh; Gowda, Vishruth; Delgado, Dioscar; Watanabe, Coran M H.

Biochemistry ; 56(6): 805-808, 2017 02 14.

Article in English | MEDLINE | ID: mdl-28135072

ABSTRACT

The biosynthesis of the azabicyclic ring system of the azinomycin family of antitumor agents represents the "crown jewel" of the pathway and is a complex process involving at least 14 enzymatic steps. This study reports on the first biosynthetic step, the inroads, in the construction of the novel aziridino [1,2-a]pyrrolidine, azabicyclic core, allowing us to support a new mechanism for azabicycle formation.

Subject(s)

Aldehyde Oxidoreductases/metabolism , Amino-Acid N-Acetyltransferase/metabolism , Antineoplastic Agents, Alkylating/metabolism , Azabicyclo Compounds/metabolism , Bacterial Proteins/metabolism , Drug Design , Phosphotransferases (Carboxyl Group Acceptor)/metabolism , Pyrrolidines/metabolism , Acetyl Coenzyme A/metabolism , Acetylation , Aldehyde Oxidoreductases/genetics , Amino-Acid N-Acetyltransferase/genetics , Antibiotics, Antineoplastic/chemistry , Antibiotics, Antineoplastic/metabolism , Antibiotics, Antineoplastic/pharmacology , Antineoplastic Agents, Alkylating/chemistry , Antineoplastic Agents, Alkylating/pharmacology , Azabicyclo Compounds/chemistry , Azabicyclo Compounds/pharmacology , Bacterial Proteins/genetics , Biocatalysis , Dipeptides/chemistry , Dipeptides/metabolism , Dipeptides/pharmacology , Gene Knockout Techniques , Glutamic Acid/metabolism , Intercellular Signaling Peptides and Proteins , Molecular Structure , Mutation , Naphthalenes/chemistry , Naphthalenes/metabolism , Naphthalenes/pharmacology , Peptides/chemistry , Peptides/metabolism , Peptides/pharmacology , Phosphotransferases (Carboxyl Group Acceptor)/genetics , Pyrrolidines/chemistry , Pyrrolidines/pharmacology , Recombinant Proteins/metabolism , Streptomyces/enzymology , Streptomyces/metabolism , Substrate Specificity

ABSTRACT

Subject(s)

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