title: 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.
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.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi della Calabria, Via P. Bucci Cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.
authors.forename: M L
authors.initials: ML
authors.lastname: Di Gioia
authors.forename: A
authors.initials: A
authors.lastname: Leggio
authors.forename: A
authors.initials: A
authors.lastname: Le Pera
authors.forename: C
authors.initials: C
authors.lastname: Siciliano
authors.forename: A
authors.initials: A
authors.lastname: Liguori
authors.forename: G
authors.initials: G
authors.lastname: Sindona
mesh_terms: D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D017607:Aluminum Compounds; D000596:Amino Acids; D000814:Aniline Compounds; D002712:Chlorides; D004151:Dipeptides; D004952:Esters; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D000077410:Aluminum Chloride