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 ( d 4-folic acid) was prepared by mixed anhydride coupling of N10-trifluoroacetylpteroic acid and dimethyl l-[3,3,4,4- 2H 4]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 C9N10 bond cleavage. A method was devised for determination of isotopic enrichment of urinary d 4-folates derived from orally administered d 4-folic acid using affinity chromatographic purification, chemical cleavage of the C9N10 bond, HPLC isolation of the p-[ 2H 4]aminobenzoylglutamate product, followed by negative-ion chemical-ionization gas chromatography/mass spectrometry. Data concerning the urinary excretion of d 4-folates derived from an oral dose of d 4-folic acid in an adult human are presented.
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