Pteroyl glutamate

Several quinoxaline analogs of pteroic acid (114) and pteroyl-glutamic acid (115) have been prepared. " - Quinoxaline-2-aldehyde,... 

The active form of fohc acid (pteroyl glutamate) is tetrahydrofolate (Figure 45-15). The folates in foods may have up to seven additional glutamate residues linked by y-peptide bonds. In addition, all of the one-carbon substituted folates in Figure 45-15 may also be present in foods. 

R12. Ross, J. F., Belding, H. W., and Paegel, B. L., Development and progression of subacute combined degeneration of spinal cord in patients with pernicious anemia treated with synthetic pteroyl glutamic (folic) acid. Blood 3, 68-90 (1948). 

N- (3,5-Dichloro-4 [ (2,4-diamino-6-pteridinyl) methyl] methylamino benzoyl) -L-glutamic acid, 4-amino-10-methyl-3, 5 -dichloro-pteroyl glutamic acid, NSC 29630. 

Synonyms cas 59-30-3 /-n-(p-(((-2-amino-4-hydroxy-6-pteridinyl) methyl>amino)BENZOYL)glutamicacid FOLACIN FOLATE FOLCYSTEINE PTEGLU PTEROYLGLUTAMC ACID PTEROYL-/-GLUTAMIC ACID PTEROYLMONOGLUTAMICACID PTEROYL-/-MONOGLUTAMIC ACID VITAMIN BC VITAMIN M... 

Pteroyl glutamic acid - folic acid (PteGlu) (FA)... 

Also among these derivatives is pteroyl-glutamic acid or folic acid, so called because of its abundant distribution in the leaves of plants. Folic add is the imiversal coenzyme for the transfer of Ci fragments and hence is indispensable for the s mthesis of purines and nucleic acids. 

Folic acid or folate (Fig. 1) is the collective name for more than 100 derivatives of pteroyl-mono-L-gluta-mate. In plant and animal tissues, folic acid mostly occurs as pteroyloligo-L-glutamate (PteGluJ, with up to eight glutamyl residues. 

Fio. 47. Retention factors of pteroyl-oliso-yL-glutamates as a ftinction of the eluent pH. The solid lines were calculated as diKussed in Bush et at. (204). Data were obtained for folic acid (FA) and oligo yglutainates containing one (Ft Glu,), three (Ft GIU ). hve (Ft GtU ), and seven (Ft Glur) utamyl residues. The data were obtained on 5 Partisil ODS-2 with 0.1 M phosphate buffers containing 696 (v/v) acetonitrile as eluent, 4S C, with detection at 254 nra. Reprinted with permission from Bush rf a/. (204). 

The mode of action of sulfanilamides became known around 1947, when the structure and biosynthesis of folic acid were elucidated. This compound is built by bacteria from the heterocyclic pteroyl moiety, p-aminobenzoate, and glutamate. p-Aminobenzene-sulfonamide (9.89, sulfanilamide) is a competitive inhibitor of the synthase enzyme, acting as an antimetabolite of p-aminobenzoate. Occasionally, the sulfanilamide can even be incorporated into the modified folate, resulting in an inactive compound and thus an inactive enzyme. This theory, proposed by Woods and Fildes in 1940, became the first molecular explanation of drug action. 

As shown in Figure 10.1, folic acid consists of a pteridine linked at C-9 to p-aminobenzoic acid, forming pteroic acid. The carboxyl group of the p-aminobenzoic acid moiety is linked by a peptide bond to the amino group of glutamate, forming pteroyl monoglutamate. 

Both pteroyl-a-glutamic acid and pteroyl-y-glutamic acid inhibit 5-methyltetrahydropteroyltriglutamate-homocysteine methyltransferase. 

Suster et al. [231] have described several AMT and MTX analogues with hydrophobic amino acid spacers between the pteroyl and glutamate moieties. Condensation of ethyl glycinate with 4-(A-Cbz-amino)benzoyl chloride, followed by alkaline hydrolysis of the ester group, DCC coupling to diethyl... 

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