Literature DB >> 21435937

Synthesis of the α,ω-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway.

John E Cronan1, Steven Lin.   

Abstract

Biotin synthesis requires the C7 α,ω-dicarboxylic acid, pimelic acid. Although pimelic acid was known to be primarily synthesized by a head to tail incorporation of acetate units, the synthetic mechanism was unknown. It has recently been demonstrated that in most bacteria the biotin pimelate moiety is synthesized by a modified fatty acid synthetic pathway in which the biotin synthetic intermediates are O-methyl esters disguised to resemble the canonical intermediates of the fatty acid synthetic pathway. Upon completion of the pimelate moiety, the methyl ester is cleaved. A very restricted set of bacteria have a different pathway in which the pimelate moiety is formed by cleavage of fatty acid synthetic intermediates by BioI, a member of the cytochrome P450 family.
Copyright © 2011 Elsevier Ltd. All rights reserved.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21435937      PMCID: PMC3110577          DOI: 10.1016/j.cbpa.2011.03.001

Source DB:  PubMed          Journal:  Curr Opin Chem Biol        ISSN: 1367-5931            Impact factor:   8.822


  26 in total

1.  THE GROWTH-STIMULATING EFFECT OF BIOTIN FOR THE DIPHTHERIA BACILLUS IN THE ABSENCE OF PIMELIC ACID.

Authors:  V DU Vigneaud; K Dittmer; E Hague; B Long
Journal:  Science       Date:  1942-08-21       Impact factor: 47.728

2.  Expression of Vibrio harveyi acyl-ACP synthetase allows efficient entry of exogenous fatty acids into the Escherichia coli fatty acid and lipid A synthetic pathways.

Authors:  Yanfang Jiang; Rachael M Morgan-Kiss; John W Campbell; Chi Ho Chan; John E Cronan
Journal:  Biochemistry       Date:  2010-02-02       Impact factor: 3.162

3.  Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis.

Authors:  J E Stok; J De Voss
Journal:  Arch Biochem Biophys       Date:  2000-12-15       Impact factor: 4.013

Review 4.  The enzymatic biotinylation of proteins: a post-translational modification of exceptional specificity.

Authors:  A Chapman-Smith; J E Cronan
Journal:  Trends Biochem Sci       Date:  1999-09       Impact factor: 13.807

5.  Integrating structure, bioinformatics, and enzymology to discover function: BioH, a new carboxylesterase from Escherichia coli.

Authors:  Ruslan Sanishvili; Alexander F Yakunin; Roman A Laskowski; Tatiana Skarina; Elena Evdokimova; Amanda Doherty-Kirby; Gilles A Lajoie; Janet M Thornton; Cheryl H Arrowsmith; Alexei Savchenko; Andrzej Joachimiak; Aled M Edwards
Journal:  J Biol Chem       Date:  2003-05-05       Impact factor: 5.157

6.  Synthesis of 7-oxo-8-aminopelargonic acid, a biotin vitamer, in cell-free extracts of Escherichia coli biotin auxotrophs.

Authors:  M A Eisenberg; C Star
Journal:  J Bacteriol       Date:  1968-10       Impact factor: 3.490

7.  Origin of carbon atoms of biotin. 13C-NMR studies on biotin biosynthesis in Escherichia coli.

Authors:  O Ifuku; H Miyaoka; N Koga; J Kishimoto; S Haze; Y Wachi; M Kajiwara
Journal:  Eur J Biochem       Date:  1994-03-01

8.  Structural insights from a P450 Carrier Protein complex reveal how specificity is achieved in the P450(BioI) ACP complex.

Authors:  Max J Cryle; Ilme Schlichting
Journal:  Proc Natl Acad Sci U S A       Date:  2008-10-06       Impact factor: 11.205

9.  Role of the active site cysteine of DpgA, a bacterial type III polyketide synthase.

Authors:  Claire C Tseng; Shaun M McLoughlin; Neil L Kelleher; Christopher T Walsh
Journal:  Biochemistry       Date:  2004-02-03       Impact factor: 3.162

10.  Use of bio-lac fusion strains to study regulation of biotin biosynthesis in Escherichia coli.

Authors:  D F Barker; A M Campbell
Journal:  J Bacteriol       Date:  1980-08       Impact factor: 3.490

View more
  15 in total

Review 1.  Fatty acid biosynthesis revisited: structure elucidation and metabolic engineering.

Authors:  Joris Beld; D John Lee; Michael D Burkart
Journal:  Mol Biosyst       Date:  2014-10-31

2.  Structure-Based Optimization of Pyridoxal 5'-Phosphate-Dependent Transaminase Enzyme (BioA) Inhibitors that Target Biotin Biosynthesis in Mycobacterium tuberculosis.

Authors:  Feng Liu; Surendra Dawadi; Kimberly M Maize; Ran Dai; Sae Woong Park; Dirk Schnappinger; Barry C Finzel; Courtney C Aldrich
Journal:  J Med Chem       Date:  2017-06-22       Impact factor: 7.446

3.  A Francisella virulence factor catalyses an essential reaction of biotin synthesis.

Authors:  Youjun Feng; Brooke A Napier; Miglena Manandhar; Sarah K Henke; David S Weiss; John E Cronan
Journal:  Mol Microbiol       Date:  2013-12-09       Impact factor: 3.501

Review 4.  Biotin biosynthesis in Mycobacterium tuberculosis: physiology, biochemistry and molecular intervention.

Authors:  Wanisa Salaemae; Al Azhar; Grant W Booker; Steven W Polyak
Journal:  Protein Cell       Date:  2011-09       Impact factor: 14.870

5.  Using the pimeloyl-CoA synthetase adenylation fold to synthesize fatty acid thioesters.

Authors:  Menglu Wang; Lucile Moynié; Peter J Harrison; Van Kelly; Andrew Piper; James H Naismith; Dominic J Campopiano
Journal:  Nat Chem Biol       Date:  2017-04-17       Impact factor: 15.040

6.  The pimeloyl-CoA synthetase BioW defines a new fold for adenylate-forming enzymes.

Authors:  Paola Estrada; Miglena Manandhar; Shi-Hui Dong; Jaigeeth Deveryshetty; Vinayak Agarwal; John E Cronan; Satish K Nair
Journal:  Nat Chem Biol       Date:  2017-04-17       Impact factor: 15.040

7.  Fatty acid biosynthesis in Pseudomonas aeruginosa is initiated by the FabY class of β-ketoacyl acyl carrier protein synthases.

Authors:  Yanqiu Yuan; Meena Sachdeva; Jennifer A Leeds; Timothy C Meredith
Journal:  J Bacteriol       Date:  2012-06-29       Impact factor: 3.490

8.  Pseudomonas aeruginosa directly shunts β-oxidation degradation intermediates into de novo fatty acid biosynthesis.

Authors:  Yanqiu Yuan; Jennifer A Leeds; Timothy C Meredith
Journal:  J Bacteriol       Date:  2012-06-29       Impact factor: 3.490

9.  Development of biotin-prototrophic and -hyperauxotrophic Corynebacterium glutamicum strains.

Authors:  Masato Ikeda; Aya Miyamoto; Sumire Mutoh; Yuko Kitano; Mei Tajima; Daisuke Shirakura; Manami Takasaki; Satoshi Mitsuhashi; Seiki Takeno
Journal:  Appl Environ Microbiol       Date:  2013-05-24       Impact factor: 4.792

10.  Brucella BioR regulator defines a complex regulatory mechanism for bacterial biotin metabolism.

Authors:  Youjun Feng; Jie Xu; Huimin Zhang; Zeliang Chen; Swaminath Srinivas
Journal:  J Bacteriol       Date:  2013-05-31       Impact factor: 3.490

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.