Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450BM₃ demethylases
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...
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Published in | Proceedings of the National Academy of Sciences - PNAS Vol. 106; no. 39; pp. 16550 - 16555 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
United States
National Academy of Sciences
29.09.2009
National Acad Sciences |
Subjects | |
Online Access | Get full text |
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Summary: | 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 (P450BM₃) 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. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 Author contributions: J.C.L., W.A.G., C.-H.W., and F.H.A. designed research; J.C.L., S.B., C.S.B., Y.M., and M.M.C. performed research; J.C.L., C.S.B., and Y.F. contributed new reagents/analytic tools; J.C.L., S.B., Y.M., and M.M.C. analyzed data; and J.C.L. and F.H.A. wrote the paper. 2Present address: Discovery Research Laboratories, Shionogi and Co. Ltd., 2–5-1 Mishima, Setu, Osaka 566-0022, Japan. Contributed by Frances H. Arnold, August 10, 2009 1Present address: Department of Chemistry, Pearson Chemistry Laboratory, Tufts University, Medford MA, 02155. |
ISSN: | 0027-8424 1091-6490 |
DOI: | 10.1073/pnas.0908954106 |