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 AlCl3/N,N-Dimethylaniline Reagent System

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 AlCl3/N,N‐dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-11, Vol.2004 (21), p.4437-4441
Main Authors: Di Gioia, Maria Luisa, Leggio, Antonella, Le Pera, Adolfo, Liguori, Angelo, Perri, Francesca, Siciliano, Carlo
Format: Article
Language:English
Subjects:
Aluminium trichloride
Amino acids
Deprotection
Dipeptides
N,N‐Dimethylaniline
N-Dimethylaniline
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Summary: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 AlCl3/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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400321