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)

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 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

• Language:English Provider:SigmaAldrich

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.

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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