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Chirality Control in Enzyme-Catalyzed Dynamic Kinetic Resolution of 1,3-Oxathiolanes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2015 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, no 16, 8478-8481 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2015. Vol. 80, no 16, 8478-8481 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-173775DOI: 10.1021/acs.joc.5b01585ISI: 000360103000072PubMedID: 26237578Scopus ID: 2-s2.0-84940069665OAI: oai:DiVA.org:kth-173775DiVA: diva2:855329
Funder
Swedish Research Council
Note

QC 20150921

Available from: 2015-09-21 Created: 2015-09-18 Last updated: 2017-12-04Bibliographically approved

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