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Catalytic dehalogenation of N‐acetyl‐L‐4‐chloro‐ and N‐acetyl‐L‐4‐iodophebylalanine amide in the presence of deuterium
Author(s) -
Oehlke J.,
Bienert M.,
Niedrich H.,
Zöpfl H.J.,
Franke P.
Publication year - 1986
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.2580230904
Subject(s) - chemistry , halogenation , deuterium , catalysis , amide , halogen , tritium , medicinal chemistry , phenylalanine , solvent , substrate (aquarium) , hydrogen–deuterium exchange , hydrogen , organic chemistry , amino acid , biochemistry , alkyl , physics , oceanography , quantum mechanics , nuclear physics , geology
As a model for the tritium labeling of peptides, the catalytic dehalogenation of N‐Acetyl‐L‐4‐chloro‐ and N‐Acetyl‐L‐4‐iodo‐phenylalanine amide was investigated in the presence of deuterium, using different reaction conditions. A catalyst‐mediated transfer of the solvent‐hydrogen to the substrate was found to be the most probable reason for the exchange of halogen by hydrogen instead of deuterium. This unwanted transter was most intensive in the presence of water. An incorporation of additional deuterium besides the 4‐position of phenylalanine takes place simultaneously with the dehalogenation especially of the chloro derivative.