Sapropterin
Title: Sapropterin
CAS Registry Number: 62989-33-7
CAS Name: (6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone
Additional Names: (6R)-L-erythro-tetrahydrobiopterin; dapropterin; R-THBP; 6R-BH4
Molecular Formula: C9H15N5O3
Molecular Weight: 241.25
Percent Composition: C 44.81%, H 6.27%, N 29.03%, O 19.90%
Literature References: Natural cofactor of the aromatic amino acid hydroxylases required for catecholamine and serotonin biosynthesis. Identification of cofactor activity: S. Kaufman, Proc. Natl. Acad. Sci. USA 50, 1085 (1963). Prepn of (6R,S)-BH4: B. Schircks et al., Helv. Chim. Acta 61, 2731 (1978). Chromatographic separation of diastereoisomers: S. W. Bailey, J. E. Ayling, J. Biol. Chem. 253, 1598 (1978). Absolute configuration of natural isomer: W. L. F. Armarego et al., Aust. J. Chem. 35, 785 (1982). Stereospecific synthesis: S. Matsuura et al., Heterocycles 23, 3115 (1985); H. Sakai, T. Kanai, EP 191335; eidem, US 4713454 (1986, 1987 both to Shiratori; Suntory). Bioavailability: G. Kapatos, S. Kaufman, Science 212, 955 (1981). Effect on neurotransmitter monoamine biosynthesis: S. Miwa et al., Arch. Biochem. Biophys. 239, 234 (1985). LC determn in biological samples: Y. Tani, T. Ishihara, Life Sci. 46, 373 (1990). Therapeutic potential in hyperphenylalaninemia: S. Kaufman, J. Nutr. Sci. Vitaminol, Suppl., 601 (1992).
Properties: pK¢ 5.05. uv max (0.1 N HCl): 265 nm (e 14000).
pKa: pK¢ 5.05
Absorption maximum: uv max (0.1 N HCl): 265 nm (e 14000)
 
Derivative Type: Dihydrochloride
CAS Registry Number: 69056-38-8
Manufacturers' Codes: SUN-0588
Trademarks: Biopten (Maruho)
Molecular Formula: C9H15N5O3.2HCl
Molecular Weight: 314.17
Percent Composition: C 34.41%, H 5.45%, N 22.29%, O 15.28%, Cl 22.57%
Properties: Crystals from HCl, mp 245-246° (dec). [a]D25 -6.81° (c = 0.665 in 0.1 M HCl). uv max (2 M HCl): 264 nm (e 16770).
Melting point: mp 245-246° (dec)
Optical Rotation: [a]D25 -6.81° (c = 0.665 in 0.1 M HCl)
Absorption maximum: uv max (2 M HCl): 264 nm (e 16770)
 
Therap-Cat: In treatment of hyperphenylalaninemia.
Keywords: Enzyme Cofactor.

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