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Radiolabelled amino acids: Synthesis of N G ‐mesitylenesulfonyl‐N 2 ‐[ 3 H]methyl‐arginine
Author(s) -
Landvatter Scott W.
Publication year - 1993
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580330910
Subject(s) - chemistry , arginine , tritium , amino acid , radiochemistry , stereochemistry , physics , nuclear physics , biochemistry
The N 2 ‐methyl amino acid N G ‐mesitylenesulfonyl‐[ 3 H]methylarginine has been prepared in high specific activity tritium labelled form by treating methyl N 2 ‐2,4‐dimethoxybenzyl‐N G ‐mesitylenesulfonyl‐arginate with [ 3 H]methyl iodide and silver(I) oxide. Removal of the dimethoxybenzyl group by transfer hydrogenation (4.4% formic acid in methanol/Pd black) followed by saponification gave N G ‐mesitylenesulfonyl‐[ 3 H]methylarginine in 30‐38% overall from [ 3 H]methyl iodide. This amino acid was ultimately used in the preparation of tritium labelled SK&F 107260 which is a cyclic peptide showing fibrinogen receptor antagonism.