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Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450_(BM3) demethylases

Lewis, Jared C. and Bastian, Sabine and Bennett, Clay S. and Fu, Yu and Mitsuda, Yuuichi and Chen, Mike M. and Greenberg, William A. and Wong, Chi-Huey and Arnold, Frances H. (2009) Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450_(BM3) demethylases. Proceedings of the National Academy of Sciences of the United States of America, 106 (39). pp. 16550-16555. ISSN 0027-8424. PMCID PMC2757845. doi:10.1073/pnas.0908954106.

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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.

Item Type:Article
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Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2009 National Academy of Sciences. Contributed by Frances H. Arnold, August 10, 2009 (received for review July 2, 2009); published online before print September 15, 2009. 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. This work was supported by the Jacobs Institute for Molecular Medicine (F.H.A.). J.C.L. is supported by U.S. National Institutes of Health Fellowship 1F32GM079932–01. S.B. was supported by the Deutsche Forschungsgemeinschaft (DFG) Grant no. BA3486/1–1. C.H.W, C.S.B., Y.F., and W.A.G. were supported by the U.S. National Institutes of Health Grants GM044154 and AI072155. C.S.B. also was supported by the U.S. National Institutes of Health Fellowship 1F32GM073500–02S01.
Funding AgencyGrant Number
Jacobs Institute for Molecular MedicineUNSPECIFIED
NIH Predoctoral Fellowship1F32GM079932–01
Deutsche Forschungsgemeinschaft (DFG)BA3486/1–1
NIH Predoctoral Fellowship1F32GM073500–02S01
Subject Keywords:biocatalysis; demethylation; evolution; P450; polysaccharide
Issue or Number:39
PubMed Central ID:PMC2757845
Record Number:CaltechAUTHORS:20091020-094419644
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:16390
Deposited On:20 Oct 2009 20:21
Last Modified:08 Nov 2021 23:26

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