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Asymmetric tritiation of N‐acetyl α‐β dehydrotryptophanamide
Author(s) -
PintoAlphandary H.,
Van CraeynestJimonet C.,
Morgat J. L.,
Fromageot P.
Publication year - 1988
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.2580251114
Subject(s) - chemistry , dehydrogenation , tritium , enantiomer , catalysis , enantiomeric excess , labelling , double bond , substrate (aquarium) , stereoselectivity , rhodium , homogeneous , enantioselective synthesis , stereochemistry , selectivity , medicinal chemistry , organic chemistry , biochemistry , physics , oceanography , geology , nuclear physics , thermodynamics
Rhodium‐DiPAMP complex catalyzes the stereoselective addition of two tritium atoms on N‐acetyl −α −β dehydrotryptophanamide. The substrate was prepared by dehydrogenation of N‐acetyltryptophanamide with TSO (Tryptophan‐Side Chain oxidase) from Pseudomonas . Tritiated N‐acetyl‐tryptophanamide was obtained with the theoretical specific radioactivity (58 Ci/mmole). The enantiomeric excess of the L‐diasteroisomer reached 94.4 %. 3 NMR spectra indicated the selectivity of 3 H‐labelling on the C α – C β double bond. This new approach of tritiation by homogeneous catalysis applied to tryptophanyl‐containing peptides is discussed.