scholarly journals Dideaza-5,6,7,8-Tetrahydrofolic Acid

2020 ◽  
Author(s):  
Keyword(s):  
Tetrahydrofolic Acid

scholarly journals 5-Methyl-5,6,7,8-tetrahydrofolic acid. Conformation of the tetrahydropyrazine ring.

1979 ◽  
Vol 254 (21) ◽  
pp. 10881-10884
Author(s):  
M. Poe ◽  
O.D. Hensens ◽  
K. Hoogsteen
Keyword(s):  
Tetrahydrofolic Acid

High Pressure Liquid Chromatographic Analysis of Food for Folates

1977 ◽  
Vol 60 (6) ◽  
pp. 1248-1251 ◽  
Author(s):  
Carolyn K Clifford ◽  
Andrew J Clifford
Keyword(s):  
High Pressure ◽  
Folic Acid ◽  
High Pressure Liquid Chromatographic ◽  
Relative Contribution ◽  
Coefficients Of Variation ◽  
Strong Anion Exchange ◽  
Liquid Chromatographic Analysis ◽  
Tetrahydrofolic Acid ◽  
Liquid Chromatographic ◽  
Area Response

Abstract The multiplicity of naturally occurring chemical forms of folates and the lack of technology to measure these forms individually stimulated the application of high pressure liquid chromatographic procedures to the separation and quantitation of these compounds. Optimum conditions for separating a mixture of tetrahydrofolic acid (THF), N5-methyltetrahydrafolic acid (N5-CH3-THF), dihydrofolic acid (DHF), and folic acid (FA) were established for a pellicular strong anion exchange resin (0.01 × 300 cm) and a potassium chloride gradient in phosphate buffer at pH 7.5, 40°C, flowing at 15.2 ml/hr. The order of elution was THF, N5-CH3-THF, DHF, and FA. The coefficients of variation for standard peak area responses ranged from 5 to 8%, and for retention times from 1.3 to 1.8%. Separations were dependent on the substitution on the pteridine portion of the molecule and were independent of the number of glutamic acid residues. Compounds were completely separated in less than 75 min. The smallest amount of folic acid which could be measured reliably was 0.035 nmole/10 μl placed on the column. Peak area response to each folate increased linearly to at least 0.21 nmole/10 μl. The relative contribution of each of the 4 folates to the total folate content of a number of fruit juices and foods differed markedly and may be related to the relative availability of folate from these sources.

Synthesis and biological activity of an acyclic analog of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]benzoyl]-L-glutamic acid

1990 ◽  
Vol 33 (2) ◽  
pp. 561-567 ◽  
Author(s):  
James L. Kelley ◽  
Ed W. McLean ◽  
Naomi K. Cohn ◽  
Mark P. Edelstein ◽  
David S. Duch ◽  
...  
Keyword(s):  
Biological Activity ◽  
Glutamic Acid ◽  
Acyclic Analog ◽  
Tetrahydrofolic Acid

Pterins. III. Methylation of 6-Methyl-5,6,7,8-tetrahydropterin, N-5-Demethylation of 1,3,5,6-Tetramethyl-5,6,7,8-tetrahydropterinium chloride hydrochloride and exchange of the 5-Methyl group in 5,6-Dimethyl-5,6,7,8-tetrahydropterin

1978 ◽  
Vol 31 (5) ◽  
pp. 1081 ◽  
Author(s):  
WLF Armarego ◽  
H Schou
Keyword(s):  
Sodium Hydroxide ◽  
Aqueous Ammonia ◽  
Methyl Group ◽  
Aerial Oxidation ◽  
Tetrahydrofolic Acid

Methylation of 6-methyl-5,6,7,8-tetrahydropterin (1) in the presence of sodium hydroxide furnishes 1,3,6-trimethyl-5,6,7,8-tetrahydropterinium chloride (3) which can be methylated further to yield 1,3,5,6- tetramethyl-5,6,7,8-tetrahydropterinium chloride (4). Demethylation of the latter salt occurred on a Dowex 50W/3 N-aqueous ammonia column with loss of the 5-methyl group to give the salt (3). The structures of these salts were deduced by a study of similar alkylations of authentic 1,6-dimethyl-,3,6-dimethyl- (6), 5,6-dimethyl-(15), 6,8-dimethyl-, 1,5,6-trimethyl-, and 3,5,6-trimethyl-5,6,7,8-tetrahydropterin (7), and of 6-methyl-2-methylamino-5,6,7,8-tetrahydropteridin- 4(3H)-one (10). Methylation of 5,6-dimethyl-5,6,7,8-tetrahydropterin (15), with trideuteromethyl iodide in the presence of alkali, was shown to give the tetramethylpterinium salt (4) in which considerable exchange of the 5-methyl group by a trideuteromethyl group had taken place. ��� The pterinium salts (3) and (4) were considerably more stable to aerial oxidation than 6-methyl-, 1,6-, 3,6-, 5,6-, 6,7-, 6,8-dimethyl-, and 1,5,6-trimethyl-5,6,7,8-tetrahydropterin. Loss of the 5-methyl group from the salt (4), and exchange of the 5-methyl group in the 5,6- dimethylpterin (15), allowed a mechanism for the enzymic transfer of the 5-methyl group in 5-methyl-5,6,7,8-tetrahydrofolic acid in biological methylations to be proposed.

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