2277-43-2

Basic information

• Product Name: (-)-2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]pteridine-4(1H)-one
• Synonyms: (-)-2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]pteridine-4(1H)-one;(-)-L-Neopterin;L-erythro-Neopterin;L-Neopterin
• CAS NO: 2277-43-2
• Molecular Formula: C9H11N5O4
• Molecular Weight: 0
• Mol File: 2277-43-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]pteridine-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]pteridine-4(1H)-one(2277-43-2)
• EPA Substance Registry System: (-)-2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]pteridine-4(1H)-one(2277-43-2)

Safety Data

• Hazardous Substances Data: 2277-43-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-erythro-pterin is utilized as a therapeutic agent for the treatment of phenylketonuria, a genetic disorder characterized by BH4 deficiency. This deficiency leads to the accumulation of toxic levels of phenylalanine in the body, causing severe health issues. By addressing the BH4 deficiency, L-erythro-pterin helps mitigate the symptoms and complications associated with phenylketonuria.
Used in Neurotransmitter Production:
L-erythro-pterin plays a vital role as a precursor in the synthesis of tetrahydrobiopterin (BH4), which is an essential cofactor for the production of neurotransmitters such as dopamine and serotonin. These neurotransmitters are crucial for various physiological processes, including mood regulation, cognitive function, and motor control. By supporting neurotransmitter production, L-erythro-pterin contributes to maintaining proper brain function and overall mental health.
Used in Nitric Oxide Production:
L-erythro-pterin is involved in the generation of nitric oxide, a molecule with diverse functions in the body, including vasodilation, immune response regulation, and neurotransmission. By participating in nitric oxide production, L-erythro-pterin supports various physiological processes and contributes to overall health and well-being.
Used in Immune System Regulation:
L-erythro-pterin contributes to the regulation of the immune system, which is essential for defending the body against infections and maintaining overall health. By playing a role in immune system regulation, L-erythro-pterin helps ensure the proper functioning of the body's defense mechanisms.

Upstream product

• 622-12-8 D-Arabinose phenylhydrazone 
• 4066-47-1 2,5,6-triaminopyrimidin-4(3H)-one dihydrochloride 
• 76212-28-7 4-hydroxy-6-(L-erythro-1,2,3-trihydroxypropyl)-2-(methylthio)pteridine 
• 5328-37-0 L-arabinose 

Downstream Products

• 113001-92-6 2-N,2'-O-diacetyl-1',3'-O-benzylidene-L-neopterin 

Relevant articles and documents

Pteridines: Synthesis and characteristics of 5,6-dihydro-6-(1,2,3-trihydroxypropyl)pteridines: Covalent intramolecular adducts

Various 5,6-diaminopyrimidines (1, 15, 24, 33) were condensed with the phenylhydrazones of L-(2) and D-arabinose (3) in acidic medium under N2 to give formal 5,6-dihydro-6-(1,2,3-trihydroxypropyl)pteridines (see, e.g., 4 and 5), the latter turned out to exist preferentially as intramolecular adducts, the hexahydropyrano-[3,2-g]pteridines 6, 7, 16, 17, 25, 26, and 34, formed subsequently by addition of the terminal OH group of the side-chain to the C(7)=N(8) bond of the pteridine moiety. Spectroscopically, the isomeric hexahydrofuro [3,2-g]pteridines 10, 11, 18, 19, and 35 were also detected as minor components in the equilibrium mixtures. In the 4-amino-2-(methylthio)pteridine series, crystallization of 6 and 7 led to the stereochemically pure (3S,4R,4aR,10aS)-6-amino-3,4,4a,5,10,10a-hexahydro-8-(methylthio -2H-pyrano[3,2-g]pteridine-3,4-diol (8) and its corresponding enantiomer 9, respectively. Structure 8 was proven by X-ray analysis. Acylation of the hexahydropyrano[3,2-g]pteridines yielded the more stable tri-, tetra-, and pentaacetyl derivatives 12-14, 20-23, 27-32, and 37-39 which were characterized and of which the absolute and relative configurations were determined (1H- and 13C-NMR and UV spectra, chiroptical measurements, elemental analyses).