Chirality Control in Enzyme-Catalyzed Dynamic Kinetic Resolution of 1,3-Oxathiolanes | Zendy

Lei Hu | Zendy; Yansong Ren | Zendy; Olof Ramström | Zendy

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Chirality Control in Enzyme-Catalyzed Dynamic Kinetic Resolution of 1,3-Oxathiolanes

Author(s) -

Lei Hu,

Yansong Ren,

Olof Ramström

Publication year - 2015

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.5b01585

Subject(s) - kinetic resolution , chirality (physics) , chemistry , catalysis , stereoselectivity , hydrolysis , kinetic control , solvent , nuclear magnetic resonance spectroscopy , stereochemistry , enzyme , combinatorial chemistry , organic chemistry , enantioselective synthesis , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model

The origin of enantioenrichment in enzyme-catalyzed dynamic kinetic resolution of 1,3-oxathiolane derivatives, key intermediates for asymmetric lamivudine synthesis, was elucidated. The chirality control could be determined by chiral HPLC and NOE NMR spectroscopy using a modified 1,3-oxathiolane compound obtained through enzyme-catalyzed selective hydrolysis. Solvent-dependent stereoselectivity was observed under biphasic conditions using different organic solvents with phosphate buffer.

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