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A potentially general synthesis of high specific activity specifically labelled tritiated peptides: Synthesis of [D‐3‐(2‐naphthyl)‐[2,3‐ 3 H]alanine 6 ]LHRH
Author(s) -
Parnes Howard,
Shelton Emma J.
Publication year - 1984
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.2580210308
Subject(s) - chemistry , specific activity , tritium , hydrolysis , peptide , alanine , tritiated water , peptide synthesis , chemical synthesis , enzyme , stereochemistry , amino acid , biochemistry , in vitro , physics , nuclear physics
High specific activity (43.7 Ci/mmol) D‐3‐(2‐naphthyl)‐[2,3,‐ 3 H] alanine ( 7 ) was obtained by reduction of methyl 2‐N‐acetylamino‐3‐(2‐naphthyl) acrylate ( 5 ) with carrier free tritium in the presence of (Ph 3 P) 3 RhCl followed by enzymatic resolution and hydrolysis. Reductions of 5 and other substrates catalyzed by Pd/C afforded products of low to medium specific activity (0.1–17 Ci/mmol). A synthetic approach which maximizes the specific activity, guarantees specificity of label, and may be applied toward the preparation of any tritiated (or 14 C) peptide is suggested. The synthesis of the decapeptide [D‐3‐(2‐naphthyl)‐[2,3‐ 3 H]alanine 6 ]LHRH ( 12 ) at 45.7 Ci/mmol, using this methodology, is described.