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Alternative and Chemoselective Deprotection of the α‐Amino and Carboxy Functions of N ‐Fmoc‐Amino Acid and N ‐Fmoc‐Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl 3 / N , N ‐Dimethylaniline Reagent System
Author(s) -
Di Gioia Maria Luisa,
Leggio Antonella,
Le Pera Adolfo,
Liguori Angelo,
Perri Francesca,
Siciliano Carlo
Publication year - 2004
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/ejoc.200400321
Subject(s) - chemistry , chemoselectivity , dipeptide , molar ratio , reagent , amino acid , peptide , organic chemistry , medicinal chemistry , catalysis , biochemistry
The amino and carboxy functions in N ‐Fmoc‐α‐amino acid and N ‐Fmoc‐peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl 3 / N , N ‐dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)