Abstract
Regio- and stereoselective hydroxylation of non-activated carbon atom is a very important reaction, but it remains a significant challenge in classic chemistry. Biohydroxylation provides a useful alternative, and considerable progress has been made recently in the discovery of new catalysts and the improvement of catalysis by substrate engineering. High throughput screening of microorganisms with a miniaturized system enables the fast identification of several new bacterial catalysts. One of them, Sphingomonas sp. HXN-200, exhibiting a broad substrate range, high activity, and high regio- and stereoselectivity, has been successfully used for practical hydroxylation. Substrate engineering based on “docking / protecting” group concept increases the substrate acceptance and regio- and stereoselectivity of known enzymatic systems, significantly extending the scope of biohydroxylations in organic synthesis. Directed evolution and site-directed mutagenesis of P450 monooxygenases, such as P450BM-3 and P450cam, have created enzymes with new substrate specificity, high activity, high selectivity, or high stability.
Keywords: stereoselective hydroxylation, synthons, catalysts, microorganisms, mutagenesis, screening
Current Organic Chemistry
Title: Recent Advances in Regio- and Stereoselective Biohydroxylation of Non- Activated Carbon Atoms
Volume: 8 Issue: 17
Author(s): Zhi Li and Dongliang Chang
Affiliation:
Keywords: stereoselective hydroxylation, synthons, catalysts, microorganisms, mutagenesis, screening
Abstract: Regio- and stereoselective hydroxylation of non-activated carbon atom is a very important reaction, but it remains a significant challenge in classic chemistry. Biohydroxylation provides a useful alternative, and considerable progress has been made recently in the discovery of new catalysts and the improvement of catalysis by substrate engineering. High throughput screening of microorganisms with a miniaturized system enables the fast identification of several new bacterial catalysts. One of them, Sphingomonas sp. HXN-200, exhibiting a broad substrate range, high activity, and high regio- and stereoselectivity, has been successfully used for practical hydroxylation. Substrate engineering based on “docking / protecting” group concept increases the substrate acceptance and regio- and stereoselectivity of known enzymatic systems, significantly extending the scope of biohydroxylations in organic synthesis. Directed evolution and site-directed mutagenesis of P450 monooxygenases, such as P450BM-3 and P450cam, have created enzymes with new substrate specificity, high activity, high selectivity, or high stability.
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Cite this article as:
Li Zhi and Chang Dongliang, Recent Advances in Regio- and Stereoselective Biohydroxylation of Non- Activated Carbon Atoms, Current Organic Chemistry 2004; 8 (17) . https://dx.doi.org/10.2174/1385272043369584
DOI https://dx.doi.org/10.2174/1385272043369584 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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