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Regioselective Lipase‐Catalysed Amidation of Dicarboxylic N ‐Blocked Amino Acid Diesters – Effect of the Side‐Chain Length
Author(s) -
Conde Santiago,
LópezSerrano Paloma,
Castro Ana,
Martínez Ana
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199911)1999:11<2835::aid-ejoc2835>3.0.co;2-t
Subject(s) - chemistry , regioselectivity , candida antarctica , lipase , side chain , yield (engineering) , diisopropyl ether , anhydrous , ether , stereochemistry , organic chemistry , catalysis , enzyme , materials science , polymer , metallurgy
Diethyl esters of both ( R )‐ and ( S )‐ N ‐blocked α‐aminoadipic and α‐aminopimelic acids yield exclusively the ω‐monoamide when they are subjected to amidation catalysed by the lipase B of Candida antarctica in anhydrous diisopropyl ether. These results are in contrast to the α‐monoamide yielded by the equivalent L ‐glutamic derivatives under the same experimental conditions. These results show that the length of the side chain plays a crucial role in the regioselectivity of the reaction.