C-h activation

Current Opinion in Chemical Biology

Volumn 3, Issue 1, 1999, Pages 22-27

  Holland, Herbert L ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; OXYGENASE;

BACTERIUM; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL INDUSTRY; COVALENT BOND; DEALKYLATION; HYDROXYLATION; MOLECULAR BIOLOGY; NONHUMAN; REVIEW; YEAST;

EID: 0033058009     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(99)80005-2     Document Type: Article

References (35)

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7. cam. FEBS Lett. 424:1998;271-274.
8. cam as a catalyst for selective hydroxylations is demonstrated in this paper, which presents data on five single-site mutants of the enzyme that can function with different regiospecificities.
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13. camhas, in our opinion, no foundation and is clearly erroneous.
14. Kitayama T Microbial asymmetric syntheses of 3-alkylphthalide derivatives. Tetrahedron - Asymmetry. 8:1997;3765-3774. The conversion of 2-ethylbenzoic acid to (S)-3-methylphthalide with 80% isolated yield and with >99% enantiomeric excess was achieved using Pseudomonas putida strain ATCC 12633 grown in the presence of o-toluic acid, which cuts as an inducer of the bacterially derived hydroxylase enzyme.
15. Holland HL, Kohl A, Larsen BG, Andreana P, Gu J-X Preparation of substituted (R)-2-alkanols by microbial hydroxylation. J Mol Catal B. 2:1997;L253-L255.
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21. Shet MS, Fisher CW, Estabrook RW The function of recombinant cytochrome P450s in intact Escherichia coli cells: the 17α-hydroxylation of progesterone and pregnenolone by P450c17. Arch Biochem Biophys. 339:1997;218-225. This paper presents groundwork for the potential use of recombinant P450 hydroxylases in E.coli. The co-expression in E.coli of both cytochrome P450c17 and NADPH-P450 reductase resulted in a microbial catalyst for the 17α-hydroxylation of progesterone that is apparently limited only by the availability of glucose and molecular oxygen, and the aqueous solubility of the substrate.
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24. Parikh A, Gillam EMJ, Guengerich FP Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat Biotechnol. 15:1997;784-788. The production of human cytochrome P-450's and human NADPH-P450 reductase from a single piece of DNA that produces one mRNA and two protein products has theoretical advantages over other co-expression systems, including equiμolar production of the two enzyμes and an increased likelihood of their co-location on the cell membrane. This system can potentially be developed as a general method for the study of drug metabolism by human cytochrome P450 hydroxylases.
25. Oliver CF, Modi S, Sutcliffe MJ, Primrose WU, Lian L-Y, Roberts GCK A single mutation in cytochrome P450 BM3 changes substrate orientation in a catalytic intermediate and the regiospecificity of hydroxylation. Biochemistry. 36:1997;1567-1572. The relationship between bound substrate and the haem-iron centre of the enzyme was probed using NMR analysis to estimate distances between individual protons of the substrate and the paramagnetic iron centre. This approach enabled the detection of a conformational rearrangement of substrate during the catalytic cycle of the enzyme.
26. Oliver CF, Modi S, Primrose WU, Lian L-Y, Roberts GCK Engineering the substrate specificity of Bacillus megaterium cytochrome P-450 BM3: hydroxylation of alkyl trimethylammonium compounds. Biochem J. 327:1997;537-544.
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28. cam is significant in that its extension to other cytochrome P450 enzymes may facilitate prediction of the outcome of the oxidative metabolism of pharmaceuticals and other xenobiotic compounds.
29. cam substrate specificity: relationship between structure and catalytic oxidation of alkylbenzenes. Arch Biochem Biophys. 353:1998;285-296.
30. Holland HL, Allen LJ, Chernishenko MJ, Diez M, Kohl A, Ozog J, Gu JX Side chain oxidation of aromatic compounds by fungi. 7. A rationale for sulfoxidation. Benzylic hydroxylation and olefin oxidation by Mortierella isabellina. J Mol Catal B. 3:1997;311-324. The active site model described in this paper is significant in that it serves as a template for the rationalisation of three disparate manifestations of hydroxylase activity: C-H hydroxylation, the conversion of sulfides to sulfoxides and the epoxidation of olefins.
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33. Cerniglia CE Fungal metabolism of polycyclic aromatic hydrocarbons: past, present and future applications in bioredemiation. J Ind Microbiol Biotechnol. 19:1997;324-333.
34. Holland HL Investigation of the carbon- and sulfur-oxidizing capabilities of microorganisms by active-site modeling. Adv Appl Microbiol. 44:1997;125-165.
35. Holland HL: Hydroxylation and dihydroxylation. In Biotechnology. Edited by Kelly DR. Weinheim: Wiley-VCH; Rehm H-J, Reed G (Series Editors): Biotransformations, vol 8a:475-533.