Neopterin
Title: Neopterin
CAS Registry Number: 670-65-5
CAS Name: 2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone
Additional Names: 1-(2-amino-4-hydroxy-6-pteridinyl)-1,2,3-propanetriol; 6-(1¢,2¢,3¢-trihydroxy)pterin; Crithidia factor
Molecular Formula: C9H11N5O4
Molecular Weight: 253.21
Percent Composition: C 42.69%, H 4.38%, N 27.66%, O 25.27%
Literature References: Precursor in the biosynthesis of biopterin, q.v. Of the four possible isomers, D-erythro, L-erythro, D-threo, L-threo, two have been found in nature: the D-erythro form, to which the term neopterin originally referred; first isolated from the pupae of bees: Rembold, Buschmann, Ann. 662, 72 (1963); the L-threo form, found to be the growth factor for the protozoan Crithidia fasciculata and isolatable from cell-free extracts of Serratia indica: Kobashi, Iwai, Agric. Biol. Chem. 35, 47 (1971); 36, 1685, 1695 (1972). Both natural forms found in human urine: Fukushima, Shiota, J. Biol. Chem. 247, 4549 (1972). Early synthetic studies and structure: Rembold, Buschmann, Ber. 96, 1406 (1963). Synthesis of L-(-)-form: Viscontini, Provenzale, Helv. Chim. Acta 51, 1495 (1968). Synthesis of natural D-neopterin: Viscontini et al., ibid. 53, 1202 (1970).
 
Derivative Type: D-erythro-Form
CAS Registry Number: 2009-64-5
Properties: [a]D25 +45 ± 3° (c = 0.3 in 0.1N HCl).
Optical Rotation: [a]D25 +45 ± 3° (c = 0.3 in 0.1N HCl)
 
Derivative Type: L-erythro-Form
Properties: [a]D25 -44 ± 3° (c = 0.3 in 0.1N HCl).
Optical Rotation: [a]D25 -44 ± 3° (c = 0.3 in 0.1N HCl)
 
Derivative Type: D-threo-Form
Properties: [a]D25 -92 ± 3° (c = 0.3 in 0.1N HCl).
Optical Rotation: [a]D25 -92 ± 3° (c = 0.3 in 0.1N HCl)
 
Derivative Type: L-threo-Form
Properties: Pale yellow, spiny crystals. [a]D25 +97 ± 3° (c = 0.3 in 0.1N HCl). uv max in 0.1N NaOH: 255, 363 nm (e 20,900, 7050); in 0.1N HCl: 248, 323 nm (e 11,200, 7880). Strong blue fluorescence in neutral or alkaline soln; weak fluorescence in acidic soln.
Optical Rotation: [a]D25 +97 ± 3° (c = 0.3 in 0.1N HCl)
Absorption maximum: uv max in 0.1N NaOH: 255, 363 nm (e 20,900, 7050)

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