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A potentially general synthesis of high specific activity specifically labelled tritiated peptides: Synthesis of [D-3-(2-naphthyl)-[2,3-3H]alanine6]LHRH

✍ Scribed by Howard Parnes; Emma J. Shelton

Publisher
John Wiley and Sons
Year
1984
Tongue
French
Weight
623 KB
Volume
21
Category
Article
ISSN
0022-2135

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✦ Synopsis

High specific activity (43.7 Ci/mmol) D-3-(2-naphthyl)-

[ 2,3, -3H]alanine (l) was obtained by reduction of methyl 2-N-acetylamino-3-(2-naphthyl)acrylate (5) with carrier free tritium in the presence of (Ph3P)3RhCl 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 (of 14C) peptide is suggested.

The synthesis of the decapeptide [D-3-(2-naphthyl)-[2.3-3H]alanine6]LHRH (12) at 4 5 . 7 Ci/mmol, using this methodology, is described.

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