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Regioselective Lipase-Catalysed Amidation of Dicarboxylic N-Blocked Amino Acid Diesters - Effect of the Side-Chain Length (1999)

Conde, Santiago ; López-Serrano, Paloma ; Castro, Ana ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 2835-2839

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ISSN: 1434-193X

Keywords: Dicarboxylic amino acids ; Amidation reactions ; Candida antarctica lipase ; Enzyme catalysis ; Regioselectivity ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 3 Tab.

Type of Medium: Electronic Resource

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