Chemical synthesis of deuterated folate monoglutamate and in vivo assessment of urinary excretion of deuterated folates in man
Abstract
The synthesis and in vivo application of stable-isotopically labeled folic acid was investigated to devise methods suitable for studies of folate metabolism in human subjects. Glutamate-labeled tetradeutero-pteroylglutamic acid (d4-folic acid) was prepared by mixed anhydride coupling of N10-trifluoroacetylpteroic acid and dimethyl L-(3,3,4,4-2H4)glutamic acid, saponification in sodium deuteroxide, and chromatographic purification. Retention of the isotopic label was verified by proton NMR and mass spectrometry of the para-aminobenzoylglutamic acid product of C9-N10 bond cleavage. A method was devised for determination of of isotopic enrichment of urinary d4-folates derived from orally administered d4-folic acid using affinity chromatographic purification, chemical cleavage of the C9-N10 bond, HPLC isolation of the p-(2H4)aminobenzoylglutamate product, followed by negative-ion chemical-ionization gas chromatography/mass spectrometry. Data concerning the urinary excretion of d4-folates derived from an oral dose of d4-folic acid in an adult human are presented.
- Authors:
- Publication Date:
- Research Org.:
- Univ. of Florida, Gainesville (USA)
- OSTI Identifier:
- 6902450
- Resource Type:
- Journal Article
- Journal Name:
- Anal. Biochem.; (United States)
- Additional Journal Information:
- Journal Volume: 170:1
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; FOLIC ACID; CHEMICAL PREPARATION; DEUTERIUM; EXCRETION; GAS CHROMATOGRAPHY; LIQUID COLUMN CHROMATOGRAPHY; MAN; MASS SPECTROSCOPY; METABOLISM; NUCLEAR MAGNETIC RESONANCE; ORAL ADMINISTRATION; TRACER TECHNIQUES; URINE; AMINO ACIDS; ANIMALS; AROMATICS; AZAARENES; BIOLOGICAL MATERIALS; BIOLOGICAL WASTES; BODY FLUIDS; CARBOXYLIC ACIDS; CHROMATOGRAPHY; CLEARANCE; DRUGS; HEMATINICS; HEMATOLOGIC AGENTS; HETEROCYCLIC COMPOUNDS; HYDROGEN ISOTOPES; HYDROXY COMPOUNDS; ISOTOPE APPLICATIONS; ISOTOPES; LIGHT NUCLEI; MAGNETIC RESONANCE; MAMMALS; MATERIALS; NUCLEI; ODD-ODD NUCLEI; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; PRIMATES; PTERIDINES; RESONANCE; SEPARATION PROCESSES; SPECTROSCOPY; STABLE ISOTOPES; SYNTHESIS; VERTEBRATES; VITAMIN B GROUP; VITAMINS; WASTES; 550201* - Biochemistry- Tracer Techniques
Citation Formats
Gregory, III, J F, and Toth, J P. Chemical synthesis of deuterated folate monoglutamate and in vivo assessment of urinary excretion of deuterated folates in man. United States: N. p., 1988.
Web. doi:10.1016/0003-2697(88)90094-2.
Gregory, III, J F, & Toth, J P. Chemical synthesis of deuterated folate monoglutamate and in vivo assessment of urinary excretion of deuterated folates in man. United States. https://doi.org/10.1016/0003-2697(88)90094-2
Gregory, III, J F, and Toth, J P. 1988.
"Chemical synthesis of deuterated folate monoglutamate and in vivo assessment of urinary excretion of deuterated folates in man". United States. https://doi.org/10.1016/0003-2697(88)90094-2.
@article{osti_6902450,
title = {Chemical synthesis of deuterated folate monoglutamate and in vivo assessment of urinary excretion of deuterated folates in man},
author = {Gregory, III, J F and Toth, J P},
abstractNote = {The synthesis and in vivo application of stable-isotopically labeled folic acid was investigated to devise methods suitable for studies of folate metabolism in human subjects. Glutamate-labeled tetradeutero-pteroylglutamic acid (d4-folic acid) was prepared by mixed anhydride coupling of N10-trifluoroacetylpteroic acid and dimethyl L-(3,3,4,4-2H4)glutamic acid, saponification in sodium deuteroxide, and chromatographic purification. Retention of the isotopic label was verified by proton NMR and mass spectrometry of the para-aminobenzoylglutamic acid product of C9-N10 bond cleavage. A method was devised for determination of of isotopic enrichment of urinary d4-folates derived from orally administered d4-folic acid using affinity chromatographic purification, chemical cleavage of the C9-N10 bond, HPLC isolation of the p-(2H4)aminobenzoylglutamate product, followed by negative-ion chemical-ionization gas chromatography/mass spectrometry. Data concerning the urinary excretion of d4-folates derived from an oral dose of d4-folic acid in an adult human are presented.},
doi = {10.1016/0003-2697(88)90094-2},
url = {https://www.osti.gov/biblio/6902450},
journal = {Anal. Biochem.; (United States)},
number = ,
volume = 170:1,
place = {United States},
year = {Fri Apr 01 00:00:00 EST 1988},
month = {Fri Apr 01 00:00:00 EST 1988}
}