Enantioselective synthesis of (2S)-2-amino-3-(4-hydroxy-3-phosphonophenyl)propionic acid (=3'-phosphono-L-tyrosine) and its incorporation into peptides

doi:10.1002/HLCA.19930760706

Paper

Enantioselective synthesis of (2S)-2-amino-3-(4-hydroxy-3-phosphonophenyl)propionic acid (=3'-phosphono-L-tyrosine) and its incorporation into peptides

Published Nov 3, 1993 · J. Paladino, C. Guyard, C. Thurieau

Helvetica Chimica Acta

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9

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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).

Study Snapshot

This study demonstrates the enantioselective synthesis and incorporation of the new amino acid (2S)-2-amino-3-(4-hydroxy-3-phosphonophenyl)propionic acid (3′-phosphono-L-tyrosine) into biologically active peptid

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Enantioselective synthesis of (2S)-2-amino-3-(4-hydroxy-3-phosphonophenyl)propionic acid (=3'-phosphono-L-tyrosine) and its incorporation into peptides

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