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