Biopterin

Title: Biopterin
CAS Registry Number: 22150-76-1
CAS Name: 2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4(1H)-pteridinone
Additional Names: 1-(2-amino-4-hydroxy-6-pteridinyl)-1,2-propanediol; 2-amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine; pterin HB2
Molecular Formula: C9H11N5O3
Molecular Weight: 237.22
Percent Composition: C 45.57%, H 4.67%, N 29.52%, O 20.23%
Literature References: A pteridine widely distributed in nature; naturally occurring as the L-erythro-form. Considered as a growth factor for some insects; see also Neopterin. Isoln from human urine: Patterson et al., J. Am. Chem. Soc. 77, 3167 (1955); 78, 5871 (1956); GB 814462 (1959 to Am. Cyanamid); from drosophila: H. S. Forrest, H. K. Mitchell, J. Am. Chem. Soc. 77, 4865 (1955); from queen bee jelly: Butenandt, Rembold, Z. Physiol. Chem. 311, 79 (1958). Absolute configuration: E. L. Patterson et al., J. Am. Chem. Soc. 78, 5871 (1956). Synthesis: E. L. Patterson et al., ibid. 5868; Tschesche et al., Ann. 658, 193 (1962); Rembold, Metzger, Ber. 96, 1395 (1963); Viscontini et al., Helv. Chim. Acta 55, 570, 574 (1972); B. Schircks et al., ibid. 60, 211 (1977); T. Sugimoto et al., Bull. Chem. Soc. Jpn. 53, 2344 (1980). Synthesis from neopterin: A. Kaiser, H. P. Wessel, Helv. Chim. Acta 70, 766 (1987). Biosynthesis: G. Kapatos et al., Science 213, 1129 (1981).
Properties: Minute, yellow, spherical crystals from water. Chars without melting at 250-280°. [a]D24 -50° (c = 0.4 in 0.1N HCl); [a]D24 -26° (c = 0.92 in 0.1N NaOH). uv max (0.08N HCl): 247 nm (e 11000). Soly in water: 0.7 mg/ml (20°); 4 mg/ml (90°). Soly in alc, ether, acetone, benzene: <0.1 mg/ml; in 1N NaOH, 1N HCl: >25 mg/ml. Fluoresces with a blue color in alkaline soln.
Optical Rotation: [a]D24 -50° (c = 0.4 in 0.1N HCl); [a]D24 -26° (c = 0.92 in 0.1N NaOH)
Absorption maximum: uv max (0.08N HCl): 247 nm (e 11000)
Bioresmethrin Biotin l-Sulfoxide Biperiden Biphenamine Bipiperidyl Mustard

Biopterin
Biopterin.svg
Identifiers
CAS number 22150-76-1 YesY
PubChem 445040
ChemSpider 392795 YesY
KEGG C06313 YesY
MeSH Biopterin
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C9H11N5O3
Molar mass 237.216 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Biopterin refers to a number of pterin coenzymes produced and utilised by many species including humans and animals. Biopterins and similar compounds are also found in some bacteria and fungi. Biopterins act as cofactors for aromatic amino acid hydroxylases, which produce a number of neurotransmitters including dopamine, norepinepherine, epinepherine, and seratonin. They are also required for the production of nitric oxide, which is also used in cell-cell signalling, most notably in regulating blood pressure by dilating blood vessels.