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Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450BM3 demethylases.


ABSTRACT: Polysaccharides comprise an extremely important class of biopolymers that play critical roles in a wide range of biological processes, but the synthesis of these compounds is challenging because of their complex structures. We have developed a chemoenzymatic method for regioselective deprotection of monosaccharide substrates using engineered Bacillus megaterium cytochrome P450 (P450(BM3)) demethylases that provides a highly efficient means to access valuable intermediates, which can be converted to a wide range of substituted monosaccharides and polysaccharides. Demethylases displaying high levels of regioselectivity toward a number of protected monosaccharides were identified using a combination of protein and substrate engineering, suggesting that this approach ultimately could be used in the synthesis of a wide range of substituted mono- and polysaccharides for studies in chemistry, biology, and medicine.

SUBMITTER: Lewis JC 

PROVIDER: S-EPMC2757845 | biostudies-other | 2009 Sep

REPOSITORIES: biostudies-other

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Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450BM3 demethylases.

Lewis Jared C JC   Bastian Sabine S   Bennett Clay S CS   Fu Yu Y   Mitsuda Yuuichi Y   Chen Mike M MM   Greenberg William A WA   Wong Chi-Huey CH   Arnold Frances H FH  

Proceedings of the National Academy of Sciences of the United States of America 20090915 39


Polysaccharides comprise an extremely important class of biopolymers that play critical roles in a wide range of biological processes, but the synthesis of these compounds is challenging because of their complex structures. We have developed a chemoenzymatic method for regioselective deprotection of monosaccharide substrates using engineered Bacillus megaterium cytochrome P450 (P450(BM3)) demethylases that provides a highly efficient means to access valuable intermediates, which can be converted  ...[more]

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2009-12-29 | GSE17425 | GEO