Efficient synthesis of pyrenylalanine.
An efficient synthesis of L-3-(1'-pyrenyl)alanine (Pya), a highly fluorescent amino acid, is described. The amino acid was obtained by the classical asymmetric hydrogenation of chiral 1-acetyl-3-pyrenemethylidene-6-methyl-piperazine-2,5-dione. In the proposed improved procedure mild conditions of the synthesis were applied and the final product--N-tertbutoxycarbonyl-pyrenylalanine--was obtained in good yield. Pyrenylalanine, due to its interesting photophysical properties, can be applied as a fluorescent probe in numerous biochemical and conformational studies.
Szymańska
A
A
Faculty of Chemistry, University of Gdańsk, Poland.
Wiczk
W
W
Lankiewicz
L
L
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D011721:Pyrenes / Q000138:chemical synthesis*
D005456:Fluorescent Dyes; D011721:Pyrenes; C047443:1-pyrenylalanine; D000409:Alanine