PREPARATION OF OLIGOMER-FREE N-ALPHA-FMOC AND N-ALPHA-URETHANE AMINO-ACIDS

A variety of N.alpha.-urethane blocked amino acids, in particular 9-fluorenylmethyloxycarbonyl (Fmoc) derivatives, have been synthesized by utilizing intermediate O,N-bis-trimethylsilyl-amino acids, formed in situ by treating an amino acid with trimethylsilylchloride and a base is an aprotic solvent...

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Bibliographic Details
Published inInternational journal of peptide and protein research Vol. 33; no. 5; pp. 353 - 359
Main Authors BOLIN, DR, SYTWU, HUMIEC, F, MEIENHOFER, J
Format Journal Article
LanguageEnglish
Published FREDERIKSBERG C Wiley 01.05.1989
Subjects
Biochemistry & Molecular Biology
Life Sciences & Biomedicine
Science & Technology
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Summary:A variety of N.alpha.-urethane blocked amino acids, in particular 9-fluorenylmethyloxycarbonyl (Fmoc) derivatives, have been synthesized by utilizing intermediate O,N-bis-trimethylsilyl-amino acids, formed in situ by treating an amino acid with trimethylsilylchloride and a base is an aprotic solvent. The intermediate is then reacted with an acylating agent. A general procedure is given which eliminates the oligomerization side reactions normally observed in Schotten-Baumann type methods. Protected amino acids obtained from this procedure are of high purity as judged by t.l.c., HPLC, ion exchange chromatography, and other physical parameters.
ISSN:0367-8377
DOI:10.1111/j.1399-3011.1989.tb00694.x