Article ; Online: Multigram-scale enzymatic kinetic resolution of trans-2-azidocyclohexyl acetate and chiral reversed-phase HPLC analysis of trans-2-azidocyclohexanol.
2021 Volume 34, Issue 2, Page(s) 428–437
Abstract: Lipase-catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram-scale hydrolytic kinetic ... ...
Abstract | Lipase-catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram-scale hydrolytic kinetic resolution of trans-2-azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative-scale process: temperature, organic co-solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc-Cl) derivatization protocol for 2-azidocyclohexanol, which enabled chiral reversed-phase high-performance liquid chromatography (RP-HPLC) determination of enantiomeric excess. |
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MeSH term(s) | Acetates ; Alcohols ; Chromatography, High Pressure Liquid/methods ; Lipase/chemistry ; Stereoisomerism |
Chemical Substances | Acetates ; Alcohols ; Lipase (EC 3.1.1.3) |
Language | English |
Publishing date | 2021-11-23 |
Publishing country | United States |
Document type | Journal Article ; Research Support, Non-U.S. Gov't |
ZDB-ID | 1011639-4 |
ISSN | 1520-636X ; 0899-0042 |
ISSN (online) | 1520-636X |
ISSN | 0899-0042 |
DOI | 10.1002/chir.23397 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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