An efficient and highly selective deprotection of N-Fmoc-alpha-amino acid and lipophilic N-Fmoc-dipeptide methyl esters with aluminium trichloride and N,N-dimethylaniline

M L Di Gioia; A Leggio; A Le Pera; C Siciliano; A Liguori; G Sindona

doi:10.1111/j.1399-3011.2004.00104.x

An efficient and highly selective deprotection of N-Fmoc-alpha-amino acid and lipophilic N-Fmoc-dipeptide methyl esters with aluminium trichloride and N,N-dimethylaniline

J Pept Res. 2004 Apr;63(4):383-7. doi: 10.1111/j.1399-3011.2004.00104.x.

Authors

M L Di Gioia¹, A Leggio, A Le Pera, C Siciliano, A Liguori, G Sindona

Affiliation

¹ Dipartimento di Scienze Farmaceutiche, Università degli Studi della Calabria, Via P. Bucci Cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.

PMID: 15102056
DOI: 10.1111/j.1399-3011.2004.00104.x

Abstract

A novel procedure for the deprotection of the carboxyl group of amino acid methyl esters is presented. The process is carried out by the reagent system aluminium trichloride/N,N-dimethylaniline that can successfully be applied to unblock the carboxyl moiety either of N-Fmoc-protected amino acid methyl esters and N-Fmoc-protected short dipeptide methyl esters. The chiralities of the optically pure amino acid or peptide precursors are maintained totally unchanged.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aluminum Chloride
Aluminum Compounds / chemistry*
Amino Acids / chemistry*
Aniline Compounds / chemistry*
Chlorides / chemistry*
Dipeptides / chemical synthesis*
Dipeptides / chemistry*
Esters / chemistry*
Fluorenes / chemistry*
Stereoisomerism

Substances

Aluminum Compounds
Amino Acids
Aniline Compounds
Chlorides
Dipeptides
Esters
Fluorenes
N(alpha)-fluorenylmethyloxycarbonylamino acids
Aluminum Chloride