Literature DB >> 14677956

Synthesis of (3S,5R)-carbapenam-3-carboxylic acid and its role in carbapenem biosynthesis and the stereoinversion problem.

Anthony Stapon1, Rongfeng Li, Craig A Townsend.   

Abstract

(5R)-Carbapenem-3-carboxylic acid is the simplest structurally among the naturally occurring carbapenem beta-lactam antibiotics. It is the produced from (3S,5S)-carbapenam-3-carboxylic acid utilizing a remarkable stereoinversion/desaturation process by CarC (carbapenem synthase), an alpha-ketoglutarate dependent non-heme iron oxygenase. In this communication, we demonstrate for the first time that the epimeric (3S,5R)-carbapenam-3-carboxylic acid is an intermediate in the overall catalytic cycle to the carbapenem antibiotic. The role of alpha-ketoglutarate in the stereoinversion and desaturation processes is also examined.

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Year:  2003        PMID： 14677956     DOI： 10.1021/ja037665w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

Review 1.  Catalytic Mechanisms of Fe(II)- and 2-Oxoglutarate-dependent Oxygenases.

Authors:  Salette Martinez; Robert P Hausinger
Journal:  J Biol Chem       Date:  2015-07-07       Impact factor: 5.157

2.  A high-throughput screen for the engineered production of β-lactam antibiotics.

Authors:  Ryan M Phelan; Benjamin J DiPardo; Craig A Townsend
Journal:  ACS Chem Biol       Date:  2012-03-19       Impact factor: 5.100

Review 3.  Dioxygen activation by nonheme iron enzymes with the 2-His-1-carboxylate facial triad that generate high-valent oxoiron oxidants.

Authors:  Subhasree Kal; Lawrence Que
Journal:  J Biol Inorg Chem       Date:  2017-01-10       Impact factor: 3.358

4.  Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy.

Authors:  Scott C Farrow; Jillian M Hagel; Guillaume A W Beaudoin; Darcy C Burns; Peter J Facchini
Journal:  Nat Chem Biol       Date:  2015-07-01       Impact factor: 15.040

5.  Definition of the common and divergent steps in carbapenem β-lactam antibiotic biosynthesis.

Authors:  Micah J Bodner; Rongfeng Li; Ryan M Phelan; Michael F Freeman; Kristos A Moshos; Evan P Lloyd; Craig A Townsend
Journal:  Chembiochem       Date:  2011-08-24       Impact factor: 3.164

6.  Mutational analysis of the thienamycin biosynthetic gene cluster from Streptomyces cattleya.

Authors:  Miriam Rodríguez; Luz Elena Núñez; Alfredo F Braña; Carmen Méndez; José A Salas; Gloria Blanco
Journal:  Antimicrob Agents Chemother       Date:  2011-01-24       Impact factor: 5.191

Review 7.  Convergent biosynthetic pathways to β-lactam antibiotics.

Authors:  Craig A Townsend
Journal:  Curr Opin Chem Biol       Date:  2016-09-29       Impact factor: 8.822

8.  Non-heme iron oxygenases generate natural structural diversity in carbapenem antibiotics.

Authors:  Micah J Bodner; Ryan M Phelan; Michael F Freeman; Rongfeng Li; Craig A Townsend
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419

9.  Mechanistic insights into the bifunctional non-heme iron oxygenase carbapenem synthase by active site saturation mutagenesis.

Authors:  Ryan M Phelan; Craig A Townsend
Journal:  J Am Chem Soc       Date:  2013-05-13       Impact factor: 15.419

10.  Consecutive radical S-adenosylmethionine methylations form the ethyl side chain in thienamycin biosynthesis.

Authors:  Daniel R Marous; Evan P Lloyd; Andrew R Buller; Kristos A Moshos; Tyler L Grove; Anthony J Blaszczyk; Squire J Booker; Craig A Townsend
Journal:  Proc Natl Acad Sci U S A       Date:  2015-08-03       Impact factor: 11.205
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