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Synthesis of 14 C‐ and 14 C 3 ‐labelled Org 37462
Author(s) -
Wiegerinck P. H. G.,
Hofstede L. W. H.,
Sperling F. M. G. M.,
Vader J. F.
Publication year - 2008
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.1499
Subject(s) - chemistry , alanine , amino acid , chemical synthesis , carbon 14 , stereochemistry , naphthalene , organic chemistry , in vitro , biochemistry , physics , quantum mechanics
Abstract Org 37462 (1) is the active ingredient in Orgalutran ® , an innovative product that reduces the time of treatment in in vitro fertilization from four to less than two weeks. Org 37462 is a synthetic decapeptide containing several amino acids that are unnatural in stereochemistry and/or in structure. The synthesis, starting with a ProtectingGroup‐ D ‐Ala‐resin, is a typical solid state synthesis. For the conduction of several metabolism studies, Org 37462 had to be labelled with carbon 14. It was decided to label D ‐3‐(2‐naphthyl)alanine, the last amino acid to be coupled to the resin. We report the synthesis of [ 14 C]‐ and [ 14 C 3 ]‐Org 37462, starting from 2‐bromo‐[ 14 C‐methyl]‐naphthalene and [ 14 C 2 ]‐ tert ‐butyl glycinate. Copyright © 2008 John Wiley & Sons, Ltd.