Journal
TETRAHEDRON-ASYMMETRY
Volume 22, Issue 18-19, Pages 1784-1789Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2011.10.009
Keywords
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Funding
- NSF-RUI [CHE-0848708]
- NSF-MRI [CHE-0923153]
- NSF-STEP [DUE-0856593]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0848708, 0923153] Funding Source: National Science Foundation
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Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.
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