Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 10, Pages 1511-1516Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800091
Keywords
amines; Candida antarctica lipase B; enantioselective acylation; enzymatic deacylation; enzyme catalysis
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A fully enzymatic methodology for the resolution of chiral amines has been demonstrated. Candida antarctica lipase B (CaLB)-catalyzed acylation with N-methyl- and N-phenylglycine, as well as analogues having the general formula R-1-XCH2CO2R2 (R-1 = Me, Ph; X = O, S) afforded the corresponding enantioenriched amides, which were subsequently enzymatically hydrolyzed. Surprisingly, CaLB also proved to be the catalyst of choice for this latter step. The heteroatom in the acyl donor profoundly influences both the enzymatic acylation and deacylation; the 0-substituted reagents performed best with regard to enantioselectivity as well as reaction rate in synthesis and hydrolysis.
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