Regioselective Lipase-Catalysed Amidation of Dicarboxylic N-Blocked Amino Acid Diesters – Effect of the Side-Chain Length

✍ Scribed by Santiago Conde; Paloma López-Serrano; Ana Castro; Ana Martínez

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 229 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199911)1999:11<2835::aid-ejoc2835>3.0.co;2-t

✦ Synopsis

Diethyl esters of both (R)-and (S)-N-blocked α-aminoadipic monoamide yielded by the equivalent L-glutamic derivatives under the same experimental conditions. These results show and α-aminopimelic acids yield exclusively the ωmonoamide when they are subjected to amidation catalysed that the length of the side chain plays a crucial role in the regioselectivity of the reaction. by the lipase B of Candida antarctica in anhydrous diisopropyl ether. These results are in contrast to the αone and two methylene groups, respectively) diethyl esters