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Proc Natl Acad Sci U S A. 2009 Sep 29;106(39):16550-5. doi: 10.1073/pnas.0908954106. Epub 2009 Sep 15.

Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450BM3 demethylases.

Author information

1
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.

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.

PMID:
19805336
PMCID:
PMC2757845
DOI:
10.1073/pnas.0908954106
[Indexed for MEDLINE]
Free PMC Article

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