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Preparation of pteroylglutamic acid‐3′,5′‐ 2 H 2 by acid catalyzed exchange with deuterium oxide
Author(s) -
Hachey D. L.,
Palladino L.,
Blair J. A.,
Rosenberg I. H.,
Klein P. D.
Publication year - 1978
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.2580140402
Subject(s) - chemistry , trifluoroacetic acid , deuterium , catalysis , hydrogen–deuterium exchange , mass spectrometry , medicinal chemistry , organic chemistry , hydrogen , chromatography , physics , quantum mechanics
Pteroylglutamic acid was labeled with deuterium by trifluoroacetic acid‐catalyzed exchange with deuterium oxide. The product, pteroylglutamic acid‐3′,5′‐ 2 H 2 , was selectively labeled with deuterium in the 4‐aminobenzoyl portion of the molecule; there was no evidence for isotope incorporation at C 7 or C 9 of the pteridine ring or at the glutamate residue. Isotope composition of the pteroylglutamates was determined by chemical ionization mass spectrometry following a base‐catalyzed, oxidative cleavage to either 4‐aminobenzoic acid or 4‐aminobenzoylglutamic acid. Products from the exchange reaction typically contained 1% 2 H 0 , 9% 2 H 1 , and 90% 2 H 2 isotopic species.