22150-76-1

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;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;NSC-339699
• CAS NO: 22150-76-1
• Molecular Formula: C₉H₁₁N₅O₃
• Molecular Weight: 237.22
• EINECS: 244-807-8
• Product Categories: Fluorescent Labels & Indicators;Bases & Related Reagents;Chiral Reagents;Heterocycles;Nucleotides
• Mol File: 22150-76-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: >210°C dec.
• Boiling Point: 379.74°C (rough estimate)
• Flash Point: 310.7 °C
• Appearance: Crystalline solid
• Density: 1.3472 (rough estimate)
• Vapor Pressure: 1.4E-13mmHg at 25°C
• Refractive Index: 1.7610 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly, Heated, Sonicated)
• PKA: 13.18±0.20(Predicted)
• Stability: Hygroscopic
• Merck: 13,1229
• BRN: 87860
• CAS DataBase Reference: 6-Biopterin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Biopterin(22150-76-1)
• EPA Substance Registry System: 6-Biopterin(22150-76-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UO3506000
• F: 10-23
• Hazardous Substances Data: 22150-76-1(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C9H11N5O3/c1-3(15)6(16)4-2-11-5-7(12-4)13-9(10)14-8(5)17/h2-3,6,15-16H,1H3,(H3,10,12,13,14,17)

Upstream product

• 132130-06-4 L-arabino-3,4,5-triacetoxy-1,1-bis-ethanesulfonyl-hex-1-ene 
• 6748-70-5 L-rhamnose diethyl dithioacetal 
• 24807-89-4 2,3,4,5-tetra-O-acetyl-L-rhamnose diethyl dithioacetal 
• 1104608-07-2 1-(2-amino-4-cyclohexyloxypteridin-6-yl)-1R,2S-1-hydroxy-2-(methoxymethoxy)propan 
• 62933-57-7 1',2'-O-diacetyl-L-biopterin 
• 123168-30-9 5-deoxy-L-ribose phenylhydrazone 
• 93978-94-0 5-deoxy-L-ribose 
• 4159-66-4 (R)-1-((4R,5S)-5-((S)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 160767-65-7 N₂-N,N-dimethylaminomethylene-L-neopterin 
• 141191-99-3 (3S,8S,9S,10R,13S,14S,17S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid 1-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-ynyl ester 
• 123077-73-6 (4RS,5S,6S)-1,4,5-triacetoxy-6-(trityloxy)-2-heptene 
• 38279-72-0 2,3-cyclohexylidene-5-deoxy-L-ribose 
• 95895-36-6 5-deoxy-2,3,4-O-triacetyl-L-arabinose-phenylhydrazone 
• 13039-56-0 5-deoxy-L-arabinose 

Downstream Products

• 94591-29-4 2-N-Benzoyl-1',2'-di-O-benzoylbiopterin 
• 62989-33-7 (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride 
• 62961-57-3 (6S)-tetrahydrobiopterin 
• 69056-38-8 (S)-2-Amino-6-((1R,2S)-1,2-dihydroxy-propyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one; hydrochloride 
• 69056-38-8 (R)-2-Amino-6-((1R,2S)-1,2-dihydroxy-propyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one; hydrochloride 
• 69056-38-8 Sapropterin dihydrochloride 
• 6779-87-9 7,8-dihydro-L-biopterin 
• 712-30-1 6-formylpterin 
• 948-60-7 pterine-6-carboxylic acid 
• 13214-44-3 6-formyl-7,8-dihydropterin 
• 94591-31-8 2-N-Benzoyl-1',2'-di-O-benzoyl-4-thiobiopterin 
• 164803-20-7 2'-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-biopterin 
• 186752-57-8 N²-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-2'-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-L-biopterin 
• 186752-61-4 di-N²:1'-O-acetyl-3-[2-(4-nitrophenyl)ethyl]2'-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-biopterin 

Relevant articles and documents

Pteridines. Part CVI. Isolation and characterization of limipterin (1-O-(L-erythro-biopterin-2'-yl)-β-N-acetylglucosamine) and its 5,6,7,8-tetrahydro derivative from green sulfur bacterium Chlorobium limicola f. thiosulfatophilum NCIB 8327

A new pteridine compound was isolated from green sulfur photosynthetic bacteria, Chlorobium limicola f. thiosulfatophilum NCIB 8327. The structure of this pterin derivative was established to be 1-O-(L-erythro-5,6,7,8-tetrahydropterin-2'-yl)-β-N-acetylglucosamine (1) from 1H-NMR and CD spectra as well as from various mass-spectrometric techniques and chemical-cleavage techniques. Upon acid hydrolysis of 1, equimolar amounts of biopterin (2) and N-acetylglucosamine were produced. The structure of the hydrolysis product 2 was confirmed by comparing its NMR, UV, CD, and MS and its chromatographical behavior with those of an authentic specimen. N-Acetylglucosamine was identified by an enzymatic hydrolysis experiment as well as by NMR and thin layer chromatography. Electrospray (ES), fast-atom-bombardment (FAB), and thermospray (TS) mass spectrometry of 1 yielded an MH+ at m/z 441. Periodate-oxidation experiments of the intact molecule 1 and of its hydrolysis product 2 are consistent with the proposed structure. Differential I2 oxidation experiments with the native compound showed that the in vivo oxidation state of this pterin is its tetrahydro form. We propose the trivial name 'limipterin' for this new compound.

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Chemical synthesis and purification method of biopterin (by machine translation)

The method, uses diacetyl biopterin as a raw material, to hydrolyze, with diacetyl biopterin to obtain the salpterin crude, obtained by extracting,hydrogenated,acid after the hydrolysis reaction time is short. and obtaining the methotrexate crude product, according to the method . The method is short in production cycle, cost, and suitable for industrial production. after recrystallization of the mixed solution . The method is simple,efficient, % by weight of the methotrexate aqueous solution obtained by. the method. (by machine translation)

NOVEL PROCESS FOR THE PREPARATION OF SAPROPTERIN DIHYDROCHLORIDE AND ITS KEY INTERMEDIATE, L-BIOPTERIN

The present invention relates to a novel process for the preparation of Sapropterin dihydrochloride of formula (1) and its key intermediate L-erythro-biopterin of formula (2). The present process is a simple and economically viable process for commercial production of Sapropterin dihydrochloride of formula (1) and its key intermediate L-biopterin of formula (2).