Priming of Azabicycle Biosynthesis in the Azinomycin Class of Antitumor Agents

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 az...

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Veröffentlicht in:	Biochemistry (Easton) 2017-02, Vol.56 (6), p.805-808
Hauptverfasser:	Mori, Shogo, Nepal, Keshav K, Kelly, Gilbert T, Sharma, Vasudha, Simkhada, Dinesh, Gowda, Vishruth, Delgado, Dioscar, Watanabe, Coran M. H
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetyl Coenzyme A - metabolism Acetylation Aldehyde Oxidoreductases - genetics Aldehyde Oxidoreductases - metabolism Amino-Acid N-Acetyltransferase - genetics Amino-Acid N-Acetyltransferase - metabolism Antibiotics, Antineoplastic - chemistry Antibiotics, Antineoplastic - metabolism Antibiotics, Antineoplastic - pharmacology Antineoplastic Agents, Alkylating - chemistry Antineoplastic Agents, Alkylating - metabolism Antineoplastic Agents, Alkylating - pharmacology Azabicyclo Compounds - chemistry Azabicyclo Compounds - metabolism Azabicyclo Compounds - pharmacology Bacterial Proteins - genetics Bacterial Proteins - metabolism Biocatalysis Dipeptides - chemistry Dipeptides - metabolism Dipeptides - pharmacology Drug Design Gene Knockout Techniques Glutamic Acid - metabolism Molecular Structure Mutation Naphthalenes - chemistry Naphthalenes - metabolism Naphthalenes - pharmacology Peptides - chemistry Peptides - metabolism Peptides - pharmacology Phosphotransferases (Carboxyl Group Acceptor) - genetics Phosphotransferases (Carboxyl Group Acceptor) - metabolism Pyrrolidines - chemistry Pyrrolidines - metabolism Pyrrolidines - pharmacology Recombinant Proteins - metabolism Streptomyces - enzymology Streptomyces - metabolism Substrate Specificity
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Zusammenfassung:	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.
ISSN:	0006-2960 1520-4995
DOI:	10.1021/acs.biochem.6b01108