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Improved conventional synthesis for 14 C‐labeled polyglutamates of folic acid
Author(s) -
Ferenz Catherine R.,
Graham David Y.
Publication year - 1989
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.2580270702
Subject(s) - chemistry , lactobacillus casei , enzyme , hydrolysis , folic acid , metabolism , enzymatic hydrolysis , conjugate , biochemistry , chemical synthesis , combinatorial chemistry , peptide , conjugated system , peptide synthesis , absorption (acoustics) , natural product , organic chemistry , in vitro , medicine , mathematical analysis , physics , mathematics , fermentation , acoustics , polymer
The majority of folates existing in nature are of the pteroylpolyglutamyl form and are unable to support Lactobacillus casei growth until the δ‐linked glutamyls are digested by conjugase enzymes. Most studies involving folate absorption have utilized monoglutamyl forms of folate, primarily folic acid. Synthetic pteroylpolyglutamates prepared by solid phase or conventional synthesis provided conjugated materials with which to study the absorption and metabolism of natural derivatives; however, the synthetic hepataglutamates support microbiological growth prior to enzymatic hydrolysis where as the natural conjugates do not. Incomplete purification of intermediate peptides during the synthesis would be the most likely explanation of this growth phenomenon. A modified solution synthesis has been developed which improves upon intermediate peptide condensations, increases product yields, and provides a heptapeptide which does not support microbiological growth until after enzymatic hydrolysis.