Efficient synthesis of pyrenylalanine

Citation
A. Szymanska et al., Efficient synthesis of pyrenylalanine, AMINO ACIDS, 21(3), 2001, pp. 265-270
Citations number
22
Categorie Soggetti
Biochemistry & Biophysics
Journal title
AMINO ACIDS
ISSN journal
09394451 → ACNP
Volume
21
Issue
3
Year of publication
2001
Pages
265 - 270
Database
ISI
SICI code
0939-4451(2001)21:3<265:ESOP>2.0.ZU;2-Z
Abstract
An efficient synthesis Of L-3-(1'-pyrenyl)alanine (Pya), a highly fluoresce nt amino acid, is described. The amino acid was obtained by the classical a symmetric hydrogenation of chiral 1-acetyl-3-pyrenemethylidene-6-methyl-pip erazine-2,5-dione. In the proposed improved procedure mild conditions of th e synthesis were applied and the final product - N-tert-butoxycarbonyl-pyre nylalanine - was obtained in good yield. Pyrenylalanine, due to its interes ting photophysical properties, can be applied as a fluorescent probe in num erous biochemical and conformational studies.