6-Biopterin Struktur

[S-(R,S)]-2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-on

Bezeichnung:[S-(R*,S*)]-2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-on

CAS-Nr22150-76-1

Englisch Name:6-Biopterin

CBNumberCB8691190

SummenformelC9H11N5O3

Molgewicht237.22

MOL-Datei22150-76-1.mol

Synonyma

[S-(R*,S*)]-2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-on

[S-(R*,S*)]-2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	>210°C dec.
alpha	D24 -50° (c = 0.4 in 0.1N HCl); D24 -26° (c = 0.92 in 0.1N NaOH)
Siedepunkt	379.74°C (rough estimate)
Dichte	1.3472 (rough estimate)
Brechungsindex	1.7610 (estimate)
storage temp.	2-8°C
Löslichkeit	Aqueous Acid (Slightly, Heated, Sonicated)
Aggregatzustand	White to pale yellow powder.
pka	13.18±0.20(Predicted)
Farbe	White to Light Yellow
Merck	13,1229
BRN	87860
Stabilität	Hygroscopic
CAS Datenbank	22150-76-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	UO3506000
F	10-23
HS Code	29339900
Toxizität	sln-par-dmg 10 mg/L MUREAV 128,147,84

Gefahreninformationscode (GHS)

6-Biopterin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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.
Chemische Eigenschaften
Crystalline Solid
Verwenden
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.
synthetische
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
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.
Sicherheitsprofil
Moderately toxic by ingestion andintraperitoneal routes. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

[S-(R,S)]-2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

22150-76-1, 6-Biopterin Verwandte Suche: