Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain.

Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. Research Abstract Details 

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Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. Abstract Text:

Nicholas M Llewellyn,Yanyan Li,Jonathan B Spencer,Nicholas M Llewellyn,Yanyan Li,Jonathan B Spencer,

Butirosin, an aminoglycoside antibiotic produced by Bacillus circulans, bears the unique (S)-4-amino-2-hydroxybutyrate (AHBA) side chain, which protects the antibiotic from several common resistance mechanisms. The AHBA side chain is advantageously incorporated into clinically valuable antibiotics such as amikacin and arbekacin by synthetic methods. Therefore, it is of significant interest to explore the biosynthetic origins of this useful moiety. We report here that the AHBA side chain of butirosin is transferred from the acyl carrier protein (ACP) BtrI to the parent aminoglycoside ribostamycin as a gamma-glutamylated dipeptide by the ACP:aminoglycoside acyltransferase BtrH. The protective gamma-glutamyl group is then cleaved by BtrG via an uncommon gamma-glutamyl cyclotransferase mechanism. The application of this pathway to the in vitro enzymatic production of novel AHBA-bearing aminoglycosides is explored with encouraging implications for the preparation of unnatural antibiotics via directed biosynthesis.

Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. Publishing Authors By Initials

NM Llewellyn,Y Li,JB Spencer,NM Llewellyn,Y Li,JB Spencer,

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Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Chemistry & biology

VOLUME: 14

Page Numbers: 379-86

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ISSN: 1074-5521

DAY: 27

MONTH: Apr

YEAR: 2007

Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain.

AFFILIATION: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.

Country: England

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MEDLINETA: Chem Biol

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