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 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.
Katarzyna
K
Kasperowicz-Frankowska
Anna
A
Gzik
Michał
M
Dziemidkiewicz
Beata
B
Kolesińska
Zbigniew J
ZJ
Kamiński
D000215:Acylation; D001881:Borates; D001888:Boric Acids / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004952:Esters; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry
D001881:Borates; D001888:Boric Acids; D004952:Esters; C509449:N-methylproline; D010455:Peptides; D014227:Triazines; D011392:Proline; C098759:fluoroboric acid