17377-13-8

Usage

InChI:InChI=1/C7H9N5O/c1-3-2-9-5-4(10-3)6(13)12-7(8)11-5/h2H2,1H3,(H4,8,9,11,12,13)

Upstream product

• 120483-46-7 C₇H₉⁽²⁾HN₆O 
• 70786-93-5 6-methyl-5,6,7,8-tetrahydropterin 
• 83387-39-7 C₆⁽¹³⁾CH₁₁N₅O₂ 
• 942-41-6 6-methyl-5,6,7,8-tetrahydrobopterin 
• 583-63-1 ortoquinone 
• 103422-18-0 C₇H₈⁽²⁾HN₅O 
• 120483-45-6 6-aminomethyl-7,8-dihydro-6H-pterin 
• 102069-94-3 6-methyldihydropterin hydrochloride 
• 708-75-8 2-amino-6-methylpteridin-4(1H)-one 
• 70786-93-5 C₆⁽¹³⁾CH₉N₅O 

Downstream Products

• 73573-51-0 (S)-6-methyl-5,6,7,8-tetrahydropterin 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 708-75-8 2-amino-6-methylpteridin-4(1H)-one 

Relevant academic research and scientific papers

INVESTIGATION OF 6-METHYLPTERIN ELECTROCHEMISTRY BY DUAL-ELECTRODE LIQUID CHROMATOGRAPHY/ELECTROCHEMISTRY.

An investigation of the electrochemistry of 6-methylpterin is reported. The dual-electrode amperometric detector is used in the series configuration to determine coupled electrochemical reactions in a complicated reaction scheme. Products generated at the upstream electrode are detected and voltammetrically characterized at the downstream electrode. The parallel configuration of the dual-electrode detector is used to identify the products of enzymatic, electrochemical, and chemical oxidation of 6-methyl-5,6,7,8-tetrahydropterin. The parallel configuration is also used to study the rate of tautomerization of quinonoid 6-methyldihydropterin.

The Synthesis of 6-Aminomethyl-5,6,7,8-tetrahydropterin

6-Aminomethyl-5,6,7,8-tetrahydropterin has been prepared by reduction of 2-acetamido-6-cyanopteridin-4(3H)-one to 2-acetamido-6-aminomethyl-5,6,7,8-tetrahydropteridin-4(3H)-one followed by acid hydrolysis.The hitherto undescribed 6-cyanopterin was prepared by careful hydrolysis of the 2-acetamido compound prepared by dehydration of the oxime derived from 2-acetamido-6-formylpteridin-4(3H)-one.The latter was prepared by selenium dioxide oxidation of the methyl compound.Oxidation of 6-aminomethyl-5,6,7,8-tetrahydropterin at neutral pH appears to proceed with significant side-chain loss in Tris buffer but not in phosphate buffer.

Effects of tetrahydropterines on the generation of quinones catalyzed by tyrosinase

Tetrahydrobiopterine (6BH4) can diminish the oxidative stress undergone by keratinocytes and melanocytes by reducing the o-quinones generated by the oxidation of the corresponding o-diphenols. We found that 6BH4 and their analogs reduced all the o-quinones studied. The formal potentials of different quinone/diphenol pairs indicate that the o-quinones with withdrawing groups are more potent oxidants than those with donating groups.

SYNTHESIS OF QUINONOID 6-METHYL AND 6,7-DIMETHYLDIHYDROPTERINS

Quinonoid 6-methyl and 6,7-dimethylpterins were synthesized by the chemical oxidation.Some of their properties are described.