Acylation of -Amino Esters and Hydrolysis of -Amido Esters: Candida antarctica LipaseA as a Chemoselective Deprotection Catalyst

作者：Maenpaa Harri; Kanerva Liisa T; Liljeblad Arto^*

来源：ChemCatChem, 2016, 8(6): 1226-1232.

DOI：10.1002/cctc.201501381

• acylation
• chemoselectivity
• enzyme catalysis
• kinetic resolution
• hydrolysis

N-Acylation by lipaseA from Candida antarctica (CAL-A) in ethyl butanoate was applied to the kinetic resolution of tert-butyl esters of 3-amino-3-phenylpropanoic acid (E>100), 3-amino-4-methylpentanoic acid (E>100) and 3-aminobutanoic acid (E=60) on 1.0-2.0m scale. With the N-acylated resolution products, the exceptional ability of CAL-A to hydrolyse amides and bulky tert-butyl esters was then studied. In all N-acylated tert-butyl esters, chemoselectivity favoured the amide bond cleavage. The tert-butyl ester bond was left intact with 3-amino-3-phenylpropanoate, whereas with 3-amino-4-methylpentanoate and 3-aminobutanoate the CAL-A-catalysed hydrolysis of tert-butyl ester followed the amide hydrolysis.

• 出版日期2016-3-18