Asymmetric Synthesis of (-)-fosfomycin and its Trans- (1S,2S)-diastereomer Using a Biocatalytic Reduction as the Key Step
Document Type
Article
Publication Date
1-1-2011
Publication Title
Tetrahedron Asymmetry
DOI
10.1016/j.tetasy.2011.10.009
ISSN
0957-4166
Abstract
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.
Recommended Citation
Marocco, Christian P., Erik V. Davis, Julie E. Finnell, Phung-Hoang Nguyen, Scott C. Mateer, Ion Ghiviriga, Clifford W. Padgett, Brent D. Feske.
2011.
"Asymmetric Synthesis of (-)-fosfomycin and its Trans- (1S,2S)-diastereomer Using a Biocatalytic Reduction as the Key Step."
Tetrahedron Asymmetry, 22 (18-19): 1784-1789: Elsevier.
doi: 10.1016/j.tetasy.2011.10.009 source: https://www.sciencedirect.com/science/article/pii/S0957416611005465?via%3Dihub
https://digitalcommons.georgiasouthern.edu/chem-facpubs/129
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