22150-76-1 Usage
Description
6-Biopterin, also known as L-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 and 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) and is rarely found under physiological conditions except in the epidermis of patients with the depigmentation disorder Vitiligo.
Used in Pharmaceutical Industry:
6-Biopterin is used as a growth factor for some insects and as a non-invasive biomarker for cancer. It is used for its cytotoxic properties to melanocytes in vitro, which can be useful in the study and treatment of melanoma and other skin-related conditions.
Used in Research Applications:
6-Biopterin is used as a research tool for studying the role of nitric oxide synthase (NOS) cofactors and their involvement in various biological processes. It is also used to investigate the mechanisms of melanogenesis regulation and the effects of 6-Biopterin on melanocytes.
Used in Diagnostic Applications:
6-Biopterin is used as a diagnostic marker for certain conditions, such as the depigmentation disorder Vitiligo, where it is found in the epidermis of affected patients. Its presence can help in the identification and monitoring of the disease.
Used in Chemical Research:
6-Biopterin is used as a crystalline solid in chemical research to study its properties and potential applications in various fields, including pharmaceuticals, diagnostics, and research.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 22150-76-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,1,5 and 0 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 22150-76:
(7*2)+(6*2)+(5*1)+(4*5)+(3*0)+(2*7)+(1*6)=71
71 % 10 = 1
So 22150-76-1 is a valid CAS Registry Number.
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)
22150-76-1Relevant 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
Cha,Pfleiderer,Yim
, p. 600 - 614 (1995)
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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Forrest,Mitchell
, p. 4865,4869 (1955)
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Chemical synthesis and purification method of biopterin (by machine translation)
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Paragraph 0011-0012, (2020/03/17)
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
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Page/Page column 10; 15; 23; 24, (2016/12/22)
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).
