J. Paladino, C. Guyard, C. Thurieau
Nov 3, 1993
Citations
0
Influential Citations
9
Citations
Journal
Helvetica Chimica Acta
Abstract
The asymmetric synthesis of derivatives of the new amino acid (2S)-2-amino-3-(4-hydroxy-3-phosphono-phenyl)propionic acid (3′-phosphono-L-tyrosine; Tyr [3′-PO(OH)2]) is described. The protected amino acid 13 is obtained via a Schollkopf synthesis by coupling of the rearranged ortho-phosphonophenolic side chain (see Scheme 1, 6a) with the lithiated bis-lactim ether 8 of cyclo(-D-valyl-glycyl-) (see Scheme 2). The incorporation of the protected amino acid 14 in a biologically active dodecapeptide is successfully achieved by the [(9H-fluoren-9-yl)-methoxy]carbonyl (Fmoc) strategy of solid-phase peptide synthesis. Differential protection of Tyr[3′-PO(OH)2] provides four levels of selective deprotection of, in the order, the N2-amino, the carboxyl (cleavage from the resin), the phenol, and the phosphono function ( peptide 16).