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)

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