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Anwendung der selektiven Amidspaltung zur Racematspaltung von Aminosäuren


Stierli, Friedrich; Obrecht, Daniel; Heimgartner, Heinz (1984). Anwendung der selektiven Amidspaltung zur Racematspaltung von Aminosäuren. CHIMIA International Journal for Chemistry, 38:432-435.

Abstract

A selective amide cleavage of dipeptide derivatives has been used for the resolution of N-acetylated alpha,alpha-disubstituted amino acids 3, prepared via the route in Scheme 2. Condensation of the racemic amino acids with (S)-Phe-N(CH3)2 gave the diastereomeric dipeptides 10 and 10' (Scheme 3), which were separated by flash-chromatography. Selective cleavage of the peptide bond yielded the enantiomeric amino acid derivatives 3/3' and 11/11', respectively.

Abstract

A selective amide cleavage of dipeptide derivatives has been used for the resolution of N-acetylated alpha,alpha-disubstituted amino acids 3, prepared via the route in Scheme 2. Condensation of the racemic amino acids with (S)-Phe-N(CH3)2 gave the diastereomeric dipeptides 10 and 10' (Scheme 3), which were separated by flash-chromatography. Selective cleavage of the peptide bond yielded the enantiomeric amino acid derivatives 3/3' and 11/11', respectively.

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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:1984
Deposited On:02 Jul 2014 14:38
Last Modified:05 Apr 2016 17:56
Publisher:Swiss Chemical Society
ISSN:0009-4293
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche & Co. AG, Basel

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