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Selective [ 15 N η 2 ] labelling of an N G ‐propionylated arginine derivative
Author(s) -
Kleinmaier Roland,
Gschwind Ruth M.
Publication year - 2009
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.1564
Subject(s) - chemistry , reagent , labelling , derivative (finance) , residue (chemistry) , stoichiometry , arginine , ornithine , stereochemistry , chemical synthesis , combinatorial chemistry , medicinal chemistry , amino acid , organic chemistry , biochemistry , financial economics , economics , in vitro
A straightforward convergent synthesis of [ 15 N η 2 ]‐Bz‐Arg(N η ‐propionyl)‐OEt * TFA is presented. In this approach, the guanidinylation reagent [ 15 N 2 ]‐N(boc)‐N′(propionyl)‐ S ‐methylisothiourea is reacted with the side chain amino group of the title compound's ornithine precursor. The guanidinylation step is promoted by stoichiometric addition of HgCl 2 to force completion. This method leads directly to the N G ‐acylated product and the acyl residue is principally modifiable in the last synthetic step of the guanidinylation reagent. Copyright © 2008 John Wiley & Sons, Ltd.