Synthesis of chiral triazine coupling reagents based on esters of N-alkylproline and their application in the enantioselective incorporation of D or L amino acid residue directly from racemic substrate

Esters of N-methylproline and N-allylproline were prepared and used as component for synthesis of chiral triazine based coupling reagents. N-Triazinylammonium tetrafluoroborate obtained from methylester of L-N-methylproline, 2-chloro-4,6-dimethozxy-1,3,5-triazine and tetrafluoroboric acid in the cou...

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Published inActa Poloniae pharmaceutica Vol. 71; no. 6; pp. 994 - 1003
Main Authors Kasperowicz-Frankowska, Katarzyna, Gzik, Anna, Dziemidkiewicz, Michał, Kolesińska, Beata, Kamiński, Zbigniew J
Format Journal Article
LanguageEnglish
Published Poland 01.11.2014
Subjects
Acylation
Borates
Boric Acids - chemistry
Chemistry Techniques, Synthetic
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Esters
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Proline - analogs & derivatives
Proline - chemistry
Stereoisomerism
Triazines - chemical synthesis
Triazines - chemistry
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Summary:Esters of N-methylproline and N-allylproline were prepared and used as component for synthesis of chiral triazine based coupling reagents. N-Triazinylammonium tetrafluoroborate obtained from methylester of L-N-methylproline, 2-chloro-4,6-dimethozxy-1,3,5-triazine and tetrafluoroboric acid in the coupling of rac-Z- A1a-OH with glycine methylester preferred formation of D-Z-AlaGly-OMe with L/D ratio 21/79. Coupling reagent prepared from D enantiomer of N-methylproline gave L-Z-AlaGly-OMe with L/D ratio 75/25.
Bibliography:ObjectType-Article-1
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ISSN:0001-6837