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

ChemCatChem ◽  
2016 ◽  
Vol 8 (6) ◽  
pp. 1226-1232 ◽  
Author(s):  
Harri Mäenpää ◽  
Liisa T. Kanerva ◽  
Arto Liljeblad
Keyword(s):  
Candida Antarctica ◽  
Candida Antarctica Lipase ◽  
Amino Esters ◽  
Lipase A ◽  
Hydrolysis Of

ChemInform Abstract: Preparation of Highly Enantiopure β-Amino Esters by Candida antarctica Lipase A.

ChemInform ◽  
2010 ◽  
Vol 32 (31) ◽  
pp. no-no
Author(s):  
Szilvia Gedey ◽  
Arto Liljeblad ◽  
Laszlo Lazar ◽  
Ferenc Fueloep ◽  
Liisa T. Kanerva
Keyword(s):  
Candida Antarctica ◽  
Candida Antarctica Lipase ◽  
Amino Esters ◽  
Lipase A

Preparation of highly enantiopure β-amino esters by Candida antarctica lipase A

2001 ◽  
Vol 12 (1) ◽  
pp. 105-110 ◽  
Author(s):  
Szilvia Gedey ◽  
Arto Liljeblad ◽  
László Lázár ◽  
Ferenc Fülöp ◽  
Liisa T. Kanerva
Keyword(s):  
Candida Antarctica ◽  
Candida Antarctica Lipase ◽  
Amino Esters ◽  
Lipase A

Candida antarctica lipase A—a powerful catalyst for the resolution of heteroaromatic β-amino esters

2002 ◽  
Vol 13 (21) ◽  
pp. 2383-2388 ◽  
Author(s):  
Magdolna Solymár ◽  
Ferenc Fülöp ◽  
Liisa T. Kanerva
Keyword(s):  
Candida Antarctica ◽  
Candida Antarctica Lipase ◽  
Amino Esters ◽  
Lipase A

Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters

2002 ◽  
Vol 80 (6) ◽  
pp. 565-570 ◽  
Author(s):  
Szilvia Gedey ◽  
Arto Liljeblad ◽  
László Lázár ◽  
Ferenc Fülöp ◽  
Liisa T Kanerva
Keyword(s):  
Key Words ◽  
Candida Antarctica ◽  
Diisopropyl Ether ◽  
The Other ◽  
Candida Antarctica Lipase B ◽  
Candida Antarctica Lipase ◽  
Structural Effects ◽  
Lipase B ◽  
Amino Esters ◽  
Catalyzed Reactions

The Candida antarctica lipase B-catalyzed reactions of five β-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same β-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated β-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated 1a was performed to demonstrate the usefulness of the method. Key words: lipase, interesterification, acylation, alcoholysis, resolution, β-amino esters.

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