Synthesis of pteroylglutamic acid-3',5'-/sup 2/H/sub 2/ by trifluoracetic acid catalyzed exchange with deuterium oxide

Conference · Wed Jan 01 00:00:00 EST 1975

OSTI ID:7362382

Palladino, L; Hachey, D L; Blair, J A; Rosenberg, I H; Klein, P D

Pteroylglutamic acid (1) was deuterated by trifluoroacetic acid catalyzed exchange with deuterium oxide. The product, pteroylglutamic acid-3'5'-/sup 2/H/sub 2/(2), was specifically deuterated in the aromatic protons of the p-aminobenzoyl (PABA) moiety; the protons on C/sub 7/, C9 and in the glutamic acid residue were not exchanged. Deuterium incorporation was measured by chemical ionization mass spectrometry. Pteroylglutamates were cleaved by a base-catalyzed, oxidative hydrolysis to PABA, which was converted to the methyl ester, N-trifluoroacetate for GC-CI-MS analysis. Products from the exchange typically contained 1 percent /sup 2/H/sub 0/, 9 percent /sup 2/H/sub 1/ and 90 percent /sup 2/H/sub 2/ species. The procedure may be used to label specifically various analogs of 1 with deuterium in the PABA portion of the molecule.

• Research Organization: Argonne National Lab., IL (USA)
• DOE Contract Number: W-31-109-ENG-38
• OSTI ID: 7362382
• Report Number(s): CONF-751027-9
• Resource Relation: Conference: 2. international conference on stable isotopes, Oak Brook, IL, USA, 20 Oct 1975
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
FOLIC ACID
BIOSYNTHESIS
LABELLING
BIOCHEMISTRY
CATALYSIS
DEUTERIUM
DEUTERIUM COMPOUNDS
GLUTAMIC ACID
HYDROLYSIS
PABA
PROTONS
AMINO ACIDS
BARYONS
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHEMISTRY
DECOMPOSITION
ELEMENTARY PARTICLES
FERMIONS
HADRONS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
ISOTOPES
LIGHT NUCLEI
LYSIS
NUCLEI
NUCLEONS
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PTERIDINES
SOLVOLYSIS
STABLE ISOTOPES
SYNTHESIS
VITAMIN B GROUP
VITAMINS
550200* - Biochemistry