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6-Biopterin [S-(R*,S*)]-2-amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one L-Biopterin,2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine
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6-Biopterin Basic information |
Product Name: | 6-Biopterin |
Synonyms: | [S-(R*,S*)]-2-amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one;L-Biopterin,2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine;L-Biopterin(6-Biopterin);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 |
CAS: | 22150-76-1 |
MF: | C9H11N5O3 |
MW: | 237.22 |
EINECS: | 244-807-8 |
Product Categories: | Fluorescent Labels & Indicators;Bases & Related Reagents;Chiral Reagents;Heterocycles;Nucleotides |
Mol File: | 22150-76-1.mol |
6-Biopterin Chemical Properties |
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 |
pka | 13.18±0.20(Predicted) |
form | White to pale yellow powder. |
Merck | 13,1229 |
BRN | 87860 |
CAS DataBase Reference | 22150-76-1(CAS DataBase Reference) |
Safety Information |
Hazard Codes | Xi |
Risk Statements | 36/37/38 |
Safety Statements | 26-36 |
WGK Germany | 3 |
RTECS | UO3506000 |
F | 10-23 |
HS Code | 29339900 |
Toxicity | sln-par-dmg 10 mg/L MUREAV 128,147,84 |
MSDS Information |
Provider | Language |
---|---|
SigmaAldrich | English |
6-Biopterin Usage And Synthesis |
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). L-Biopterin is rarely found under physiological conditions except in the epidermis of patients with the depigmentation disorder Vitiligo. |
Chemical Properties | Crystalline Solid |
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. |
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 |
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. |
Definition | An enzymatic cofactor derived from pterin and involved in certain oxidation-reduction reactions. |
Safety Profile | Moderately toxic by ingestion andintraperitoneal routes. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx. |
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