712-29-8

Usage

Uses

Used in Pharmaceutical Industry:
6-Hydroxymethylpterin is used as an intermediate in the synthesis of 2-Amino-6-(chloromethyl)-4(3H)-pteridinone (A602875), which is a reagent/intermediate for the preparation of Folic Acid (F680300) and its derivatives. Folic acid is an essential vitamin that plays a crucial role in cell growth, DNA synthesis, and the formation of red blood cells. It is commonly used in supplements and fortified foods to prevent neural tube defects during pregnancy and to treat folic acid deficiency anemia.
Additionally, 6-hydroxymethylpterin may be utilized in the development of other pteridine-based compounds with potential therapeutic applications, such as anti-inflammatory, anti-cancer, and antiviral agents. Its versatility as a synthetic intermediate makes it valuable in the pharmaceutical industry for creating new and innovative medications.

InChI:InChI=1/C7H7N5O2/c8-7-11-5-4(6(14)12-7)10-3(2-13)1-9-5/h1,13H,2H2,(H3,8,9,11,12,14)

Upstream product

• 712-30-1 6-formylpterin 
• 73978-41-3 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride 
• 5221-17-0 2,3-dibromopropanal 
• 96-26-4 dihydroxyacetone 
• 26944-17-2 2,2,3-tribromopropanal 
• 4066-47-1 2,5,6-triaminopyrimidin-4(3H)-one dihydrochloride 
• 7803-57-8 hydrazine hydrate 
• 1004-75-7 2,5,6-triamino-4-hydroxypyrimidine 
• 2009-64-5 D-neopterin 
• 59-30-3 folic acid 

Downstream Products

• 694514-39-1 7-hydroxymethylpterin 
• 32363-58-9 N-{6-[(acetyloxy)methyl]-3,4-dihydro-4-oxopteridin-2-yl}acetamide 
• 3672-03-5 7,8-dihydro-6-(hydroxymethyl)pterin 
• 31969-10-5 6-hydroxymethyl-5,6,7,8-tetrahydropterin dihydrochloride 
• 49754-41-8 6-hydroxymethylpterin monophosphate 
• 222612-05-7 2-{[(dimethylamino)methylene]amino}-6-(hydroxymethyl)pteridin-4(3H)-one 
• 142645-51-0 6-pivaloyloxymethyl-2-pivaloylaminopteridin-4(3H)-one 
• 948-60-7 pterin-6-carboxylic acid 
• 712-30-1 6-pterinaldehyde 
• 712-30-1 6-formylpterin 
• 948-60-7 pterine-6-carboxylic acid 
• 142645-53-2 2-(2,2-Dimethyl-propionylamino)-6-(2,2-dimethyl-propionyloxymethyl)-4-oxo-4,6,7,8-tetrahydro-3H-pteridine-5-carboxylic acid benzyl ester 
• 6863-06-5 6-hydroxymethyl-3,4-dihydropterin pyrophosphate 
• 73978-45-7 6-(Acetoxymethyl)pterin 

Relevant academic research and scientific papers

Tetrahydrofurfuroxy folic acid analogue synthetic method

The invention relates to a novel method for synthesis of tetrahydrofolic acid analogues, and mainly solves the problems of uneasily controllable reaction conditions and many produced by products in a conventional synthesis method. A series of tetrahydrofolic acid analogues are prepared by employing 5-aminouracil or 2,4,5,6-tetraaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine as an initial raw material and combining the steps of cyclization, oxidation, chlorination, ammonolysis, catalytic hydrogenation reduction, intramolecular cyclization, aziridine ring opening, nucleophilic substitution, ethoxycarbonyl hydrolysis, etc. Compared with a conventional synthesis method, the novel method provided by the invention has the characteristics of mild and stable reaction conditions, few by-products, wide application range, etc.

Comparative genomics guided discovery of two missing archaeal enzyme families involved in the biosynthesis of the pterin moiety of tetrahydromethanopterin and tetrahydrofolate

C-1 carriers are essential cofactors in all domains of life, and in Archaea, these can be derivatives of tetrahydromethanopterin (H4-MPT) or tetrahydrofolate (H4-folate). Their synthesis requires 6-hydroxymethyl-7,8-dihydropterin dip

Synthesis of 6-hydroxymethylpterin α- And β-D-glucosides

The key precursor, N2-(N,N-dimethylaminomethylene)-6-hydroxy- methyl-3-[2-(4-nitrophenyl)ethyl]pterin (11) was efficiently prepared from 2,5,6-triamino-4-hydroxypyrimidine (8) in 5 steps. The first, unequivocal synthesis of 6-hydroxymethylpteri

Bisubstrate analogue inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase: Synthesis and biochemical and crystallographic studies

6-Hydroxymethyl-7,8-dihydropterin pyrophosphokinase (HPPK) catalyzes the transfer of pyrophosphate from ATP to 6-hydroxymethyl-7,8-dihydropterin (HP), leading to the biosynthesis of folate cofactors. Like other enzymes in the folate pathway, HPPK is an ideal target for the development of antimicrobial agents because the enzyme is essential for microorganisms but is absent from human and animals. Three bisubstrate analogues have been synthesized for HPPK and characterized by biochemical and X-ray crystallographic analyses. All three bisubstrate analogues consist of a pterin, an adenosine moiety, and a link composed of 2-4 phosphoryl groups. P1-(6-Hydroxymethylpterin)-P2-(5′-adenosyl) diphosphate (HP2A, 5) shows little affinity and inhibitory activity for E. coli HPPK. P1-(6-Hydroxymethylpterin)-P3-(5′-adenosyl) triphosphate (HP3A, 6) shows moderate affinity and inhibitory activity with Kd = 4.25 μM in the presence of Mg2+ and IC50 = 1.27 μM. P1-(6-Hydroxymethylpterin)-P4-(5′-adenosyl) tetraphosphate (HP4A, 7) shows the highest affinity and inhibitory activity with Kd = 0.47 μM in the presence of Mg2+ and IC50 = 0.44 μM. The affinity of MgHP4A for HPPK is ～116 and 76 times higher than that of MgADP and 6-hydroxymethylpterin, respectively. The crystal structure of HPPK in complex with 7 (HPPK·MgHP4A) has been determined at 1.85 A? resolution with a crystallographic R factor of 0.185. The crystal structure shows that 7 occupies both HP- and ATP-binding sites and induces significant conformational changes in HPPK. The biochemical and structural studies of the bisubstrate analogues indicate that the bisubstrate analogue approach can produce more potent inhibitors for HPPK and the minimum length of the link for a bisubstrate analogue is ～7 A?.

Pteridines, LXIX. Synthesis and Reactivity of 2,4-Diamino-6-(hydroxymethyl)pteridine

Condensation of 2,4,5,6-tetraaminopyridine (2) with 1,3-dihydroxyacetone in the presence of gaseous oxygen, rather than air, resulted in 2,4-diamino-6-(hydroxymethyl)pteridine (3) virtually uncontaminated with 2,4-diamino-6-methylpteridine (4).Acetylation of 3 led to 6-acetoxymethyl-2,4-bis(acetylamino)pteridine (5) which turned out to be very labile forming various di- and monoacetyl derivatives (6, 7, 9, 10) on mild hydrolytic conditions.Their structures are proven by physical-chemical means.Silylation of 3 to the tris(trimethylsilyl) derivative 11 followed by treatment with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (12) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (15), respectively, in the presence of boron trifluoride,led to selective formation of the corresponding acylated 2,4-diamino-6-pteridinyl O-glycosides 13 and 15, respectively.Deacylations of these afforded the free O-glycosides 14 and 17 which have been characterized by UV- and NMR spectra as well as pKa measurements.