Literature DB >> 28363936

ω- versus (ω-1)-hydroxylation: Cytochrome P450 4B1 sterics make the call.

Emily E Scott1.   

Abstract

Many family 4 cytochrome P450s play key roles in fatty acid hydroxylation at the terminal, or ω, carbon, but the mechanistic basis for this energetically disfavored regiostereochemistry has been less clear. A co-crystal structure of the rabbit family 4 enzyme CYP4B1 with its substrate octane reveals that the propensity for ω-hydroxylation is orchestrated by active-site sterics, partially mediated by an unusual heme-polypeptide ester bond.
© 2017 by The American Society for Biochemistry and Molecular Biology, Inc.

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Year:  2017        PMID： 28363936      PMCID： PMC5392704          DOI： 10.1074/jbc.H117.775494

Source DB:  PubMed          Journal:  J Biol Chem        ISSN： 0021-9258            Impact factor:   5.157


  9 in total

Review 1.  CYP4B1: an enigmatic P450 at the interface between xenobiotic and endobiotic metabolism.

Authors:  Brian R Baer; Allan E Rettie
Journal:  Drug Metab Rev       Date:  2006       Impact factor: 4.518

2.  H2-driven biotransformation of n-octane to 1-octanol by a recombinant Pseudomonas putida strain co-synthesizing an O2-tolerant hydrogenase and a P450 monooxygenase.

Authors:  Thomas H Lonsdale; Lars Lauterbach; Sumire Honda Malca; Bettina M Nestl; Bernhard Hauer; Oliver Lenz
Journal:  Chem Commun (Camb)       Date:  2015-11-21       Impact factor: 6.222

3.  Generation and characterization of a Cyp4b1 null mouse and the role of CYP4B1 in the activation and toxicity of Ipomeanol.

Authors:  Oliver T Parkinson; H Denny Liggitt; Allan E Rettie; Edward J Kelly
Journal:  Toxicol Sci       Date:  2013-06-07       Impact factor: 4.849

4.  The Crystal Structure of Cytochrome P450 4B1 (CYP4B1) Monooxygenase Complexed with Octane Discloses Several Structural Adaptations for ω-Hydroxylation.

Authors:  Mei-Hui Hsu; Brian R Baer; Allan E Rettie; Eric F Johnson
Journal:  J Biol Chem       Date:  2017-02-06       Impact factor: 5.157

5.  CYP4B1 is a possible risk factor for bladder cancer in humans.

Authors:  S Imaoka; Y Yoneda; T Sugimoto; T Hiroi; K Yamamoto; T Nakatani; Y Funae
Journal:  Biochem Biophys Res Commun       Date:  2000-11-02       Impact factor: 3.575

6.  Rabbit CYP4B1 engineered for high-level expression in Escherichia coli: ligand stabilization and processing of the N-terminus and heme prosthetic group.

Authors:  Matthew J Cheesman; Brian R Baer; Yi-Min Zheng; Elizabeth M J Gillam; Allan E Rettie
Journal:  Arch Biochem Biophys       Date:  2003-08-01       Impact factor: 4.013

7.  Phase I and pharmacological study of the pulmonary cytotoxin 4-ipomeanol on a single dose schedule in lung cancer patients: hepatotoxicity is dose limiting in humans.

Authors:  E K Rowinsky; D A Noe; D S Ettinger; M C Christian; B G Lubejko; E K Fishman; S E Sartorius; M R Boyd; R C Donehower
Journal:  Cancer Res       Date:  1993-04-15       Impact factor: 12.701

8.  New prodrug activation gene therapy for cancer using cytochrome P450 4B1 and 2-aminoanthracene/4-ipomeanol.

Authors:  N G Rainov; K U Dobberstein; M Sena-Esteves; U Herrlinger; C M Kramm; R M Philpot; J Hilton; E A Chiocca; X O Breakefield
Journal:  Hum Gene Ther       Date:  1998-06-10       Impact factor: 5.695

9.  Microbial production of 1-octanol: A naturally excreted biofuel with diesel-like properties.

Authors:  M Kalim Akhtar; Hariharan Dandapani; Kati Thiel; Patrik R Jones
Journal:  Metab Eng Commun       Date:  2014-11-13
  9 in total
  4 in total

1.  Computational Insight Into Vitamin K1 ω-Hydroxylation by Cytochrome P450 4F2.

Authors:  Junhao Li; Hongxiao Zhang; Guixia Liu; Yun Tang; Yaoquan Tu; Weihua Li
Journal:  Front Pharmacol       Date:  2018-09-25       Impact factor: 5.810

2.  Transcriptome Analysis Reveals Differential Expression of Genes Regulating Hepatic Triglyceride Metabolism in Pekin Ducks During Dietary Threonine Deficiency.

Authors:  Yong Jiang; Ming Xie; Wenlei Fan; Jiajia Xue; Zhengkui Zhou; Jing Tang; Guohong Chen; Shuisheng Hou
Journal:  Front Genet       Date:  2019-08-02       Impact factor: 4.599

Review 3.  Molecular Functionality of Cytochrome P450 4 (CYP4) Genetic Polymorphisms and Their Clinical Implications.

Authors:  Yazun Bashir Jarrar; Su-Jun Lee
Journal:  Int J Mol Sci       Date:  2019-08-31       Impact factor: 5.923

4.  Cytochrome P450 168A1 from Pseudomonas aeruginosa is involved in the hydroxylation of biologically relevant fatty acids.

Authors:  Claire L Price; Andrew G S Warrilow; Nicola J Rolley; Josie E Parker; Vera Thoss; Diane E Kelly; Nicolae Corcionivoschi; Steven L Kelly
Journal:  PLoS One       Date:  2022-03-21       Impact factor: 3.240
  4 in total

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