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Optisch aktive 3-Amino-2H-azirine als Bausteine für enantiomerenreine alpha,alpha-disubstituierte alpha-Aminosäuren: Synthese des alpha-Methylphenylalanin-Synthons and Einbau in Modell-Peptide


Bucher, Christoph B; Linden, Anthony; Heimgartner, Heinz (1995). Optisch aktive 3-Amino-2H-azirine als Bausteine für enantiomerenreine alpha,alpha-disubstituierte alpha-Aminosäuren: Synthese des alpha-Methylphenylalanin-Synthons and Einbau in Modell-Peptide. Helvetica Chimica Acta, 78:935-946.

Abstract

Optically Active 3-Amino-2H-azirines as Synthons for Enantiomerically Pure alpha,alpha-Disubstituted alpha-Amino Acids: Synthesis of the alpha-Methylphenylalanine Synthons and Some Model Peptides The synthesis of a novel 2-benzyl-2-methyl-3-amino-2H-azirine derivative with a chiral amino group is described. Chromatographic separation of the diastereoisomer mixture yielded the pure diastereoisomers 9a and 9b (Scheme 4 ) which are the D- and L-2-methylphenylalanine ((alpha-Me)Phe) synthons, respectively. The reaction of 9a and 9b with thiobenzoic acid and with Z-leucine yielded the monothiodiamides 10a and 10b (Scheme 5 ) and the dipeptide derivatives 11a and 11b (Scheme 6), respectively. Methanolysis of 11b yielded 12b. The absolute configuration of 10a was established by X-ray crystallography. The absolute configuration of (alpha-Me)Phe in 12b has been deduced from the known configuration of L-leucine.

Abstract

Optically Active 3-Amino-2H-azirines as Synthons for Enantiomerically Pure alpha,alpha-Disubstituted alpha-Amino Acids: Synthesis of the alpha-Methylphenylalanine Synthons and Some Model Peptides The synthesis of a novel 2-benzyl-2-methyl-3-amino-2H-azirine derivative with a chiral amino group is described. Chromatographic separation of the diastereoisomer mixture yielded the pure diastereoisomers 9a and 9b (Scheme 4 ) which are the D- and L-2-methylphenylalanine ((alpha-Me)Phe) synthons, respectively. The reaction of 9a and 9b with thiobenzoic acid and with Z-leucine yielded the monothiodiamides 10a and 10b (Scheme 5 ) and the dipeptide derivatives 11a and 11b (Scheme 6), respectively. Methanolysis of 11b yielded 12b. The absolute configuration of 10a was established by X-ray crystallography. The absolute configuration of (alpha-Me)Phe in 12b has been deduced from the known configuration of L-leucine.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1995
Deposited On:04 Dec 2013 13:30
Last Modified:05 Apr 2016 17:12
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel

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