6-Biopterin

Synonym(s):(1’R,2’S)-Biopterin;L-erythro-6-(1,2-Dihydroxypropyl)pterin;2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine

CAS NO.：22150-76-1
Empirical Formula: C9H11N5O3
Molecular Weight: 237.22
MDL number: MFCD00036787
EINECS: 244-807-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-05 08:26:49

What is 6-Biopterin?

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

The Uses of 6-Biopterin

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.

What are the applications of Application

L-Biopterin is a cofactor in the production of many neurotransmitters and nitric oxide

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.

What are the applications of 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.

Properties of 6-Biopterin

Melting point:	>210°C dec.
Boiling point:	379.74°C (rough estimate)
alpha	D24 -50° (c = 0.4 in 0.1N HCl); D24 -26° (c = 0.92 in 0.1N NaOH)
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
CAS DataBase Reference	22150-76-1(CAS DataBase Reference)

Safety information for 6-Biopterin

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.