Basic information Safety Supplier Related

6-Biopterin

Basic information Safety Supplier Related

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
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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
solubility 
Aqueous Acid (Slightly, Heated, Sonicated)
pka
13.18±0.20(Predicted)
form 
White to pale yellow powder.
color 
White to Light Yellow
Merck 
13,1229
BRN 
87860
Stability:
Hygroscopic
CAS DataBase Reference
22150-76-1(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
UO3506000
10-23
HS Code 
29339900
Toxicity
sln-par-dmg 10 mg/L MUREAV 128,147,84

MSDS

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6-Biopterin Usage And Synthesis

Description

6-Biopterin (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

L-Biopterin is 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.

Definition

6-Biopterin is an enzymatic cofactor derived from pterin and involved in certain oxidation-reduction reactions. It is a biopterin in which the 1,2-dihydroxypropyl group has (1R,2S)-configuration; naturally occurring form. It is an enantiomer of a D-erythro-biopterin.

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.

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