| Identification | More | [Name]
6-Biopterin | [CAS]
22150-76-1 | [Synonyms]
(1'R,2'S)-BIOPTERIN
2-AMINO-4-HYDROXY-6-[1,2-DIHYDROXYPROPYL]PTERIDINE
6-BIOPTERIN
BIOPTERIN
L-BIOPTERIN
L-ERYTHRO-6-(1,2-DIHYDROXYPROPYL)PTERIN
2-amino-6-(1,2-dihydroxypropyl)-,(s-(r*,s*))-4(1h)-pteridinon
2-amino-6-(l-erythro-1,2-dihydroxypropyl)-4(3h)-pteridinon
pterinhb2
[S-(R*,S*)]-2-amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one
L-Biopterin,2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine
2-amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one
(1R,2S)-Biopterin, 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine, L-erythro-6-(1,2-Dihydroxypropyl)pterin
2-Amino-6-[(1S,2R)-1,2-dihydroxypropyl]pteridin-4(1H)-one
2-Amino-6-[(1S,2R)-1,2-dihydroxypropyl]pteridine-4(3H)-one
D-erythro-Biopterin
NSC-339699
2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4(1H)-pteridinone
2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(3H)-one
L-erythro-Biopterin | [EINECS(EC#)]
244-807-8 | [Molecular Formula]
C9H11N5O3 | [MDL Number]
MFCD00036787 | [Molecular Weight]
237.22 | [MOL File]
22150-76-1.mol |
| Chemical Properties | Back Directory | [Definition]
An enzymatic cofactor derived from pterin and involved in certain oxidation-reduction reactions. | [Appearance]
Crystalline Solid | [Melting point ]
>210°C dec. | [alpha ]
D24 -50° (c = 0.4 in 0.1N HCl); D24 -26° (c = 0.92 in 0.1N NaOH) | [Boiling point ]
379.74°C (rough estimate) | [density ]
1.3472 (rough estimate) | [refractive index ]
1.7610 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Aqueous Acid (Slightly, Heated, Sonicated) | [form ]
White to pale yellow powder. | [pka]
13.18±0.20(Predicted) | [color ]
White to Light Yellow | [Merck ]
13,1229 | [BRN ]
87860 | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1 | [InChIKey]
LHQIJBMDNUYRAM-DZSWIPIPSA-N | [SMILES]
N1C2C(=NC([C@@H](O)[C@@H](O)C)=CN=2)C(=O)N=C1N | [CAS DataBase Reference]
22150-76-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
UO3506000
| [F ]
10-23 | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Toxicity]
sln-par-dmg 10 mg/L MUREAV 128,147,84 |
| Hazard Information | Back Directory | [Description]
L-Biopterin is the oxidized form of tetrahydro-L-biopterin (BH4), a nitric oxide synthase (NOS) cofactor. L-Biopterin can be reduced to BH4 via thioredoxin reductase followed by dihydropteridine reductase or reduced glutathione. It is extremely toxic to human melanocytes in culture (IC50 = 0.2 μM after 48 hrs).1 L-Biopterin is rarely found under physiological conditions except in the epidermis of patients with the depigmentation disorder Vitiligo.2 | [Chemical Properties]
Crystalline Solid | [Uses]
6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer. | [Uses]
6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via | [Uses]
A pteridine widely distributed in nature; naturally occurring as the L-erythro-form. Considered as a growth factor for some insects. Fluoresces with a blue color in alkaline solution. | [Application]
6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer. | [Preparation]
Biopterin is synthesized by reacting 2,4,5-triamino-6-hydroxypyrimidine with 5-deoxy-L-arabinosone in aqueous solution at pH of about 7.5 to 10, acidifying and then recrystallizing by dissolving in basic solution and precipitating with acid. 5-deoxy-L-arabinosone is prepared by oxidizing S-deoxy-L-arabinose, which is prepared from L-rhamnose, using cupric acetate.
Process for the synthesis of biopterin | [Safety Profile]
Moderately toxic by ingestion andintraperitoneal routes. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx. | [References]
[1] SCHALLREUTER K.U. Cytotoxicity of 6-Biopterin to Human Melanocytes[J]. Biochemical and biophysical research communications, 1994, 204 1: Pages 43-48. DOI: 10.1006/bbrc.1994.2423
[2] JEREMY MOORE Karin U S John M Wood. Evidence for Specific Complex Formation between α-Melanocyte Stimulating Hormone and 6(R)-l-Erythro-5,6,7,8-tetrahydrobiopterin using Near Infrared Fourier Transform Raman Spectroscopy?[J]. Biochemistry Biochemistry, 1999, 38 46: 15317-15324. DOI: 10.1021/bi991448j |
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