(6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE

Base Information

• Chemical Name: (6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE
• CAS No.: 69056-38-8
• Molecular Formula: C₉H₁₅N₅O₃*2ClH
• Molecular Weight: 314.172
• Hs Code.: 2933990090
• Mol file: 69056-38-8.mol

Synonyms:4(1H)-Pteridinone,2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-, dihydrochloride,[6R-[6R*(1R*,2S*)]]-;4(1H)-Pteridinone,2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-, dihydrochloride,(6R)- (9CI);Sapropterindihydrochloride;

Chemical Property of (6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 2.2E-12mmHg at 25°C
• Melting Point: 245-246° (dec)
• Boiling Point: 506.6 °C at 760 mmHg
• Flash Point: 260.2 °C
• PSA: 136.29000
• LogP: 0.76100
• Storage Temp.: −20°C
• Solubility.: water, oxygen free: soluble19.60 - 20.40mg/mL, clear to slightly

Purity/Quality:

99% ^*data from raw suppliers

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Description: Sapropterin hydrochloride is a monoamine biosynthesis enhancer introduced for the treatment of hyperphenylalaninemia.Animal studies indicate that sapropterin hydrochloride increases brain levels of serotonin and enhances the release of acetylcholine from nerve terminals. The compound is also being investigated as a potential cognitive enhancer. (6R)-5,6,7,8-tetrahydro-L-Biopterin (hydrochloride) (BH4) is a cofactor that, in the presence of enzyme site iron, binds to phenylalanine hydroxylase, tryptophan or tyrosine hydroxylase, and nitric oxide synthase (NOS), to facilitate the production of aromatic amino acids, neurotransmitters, and nitric oxide (NO), respectively. It is formed de novo from GTP with GTP cyclohydrolase-1 (GCH1) catalyzing the rate limiting conversion of GTP to 7,8-dihydroneopterin (NH2TP) followed by subsequent processing by TS and SPR to convert NH2TP to BH4. BH4 acts as a radical-trapping antioxidant that inhibits phospholipid oxidation in lipid membranes. It inhibits IKE- or RSL3-induced ferroptosis in HT-1080 cells (EC50s = 21 and 69 μM), as well as ferroptosis induced by knockout of glutathione peroxidase (Gpx4-/-) in immortalized mouse fibroblasts. BH4 also reduces RLS3-induced lipid peroxidation in murine fibroblasts and HT-1080 cells when used at a concentration of 50 μM.

Technology Process of (6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE

There total 11 articles about (6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

C11H15N5O4 → Sapropterin dihydrochloride (69056-38-8,69056-39-9,71074-53-8,83023-72-7,83709-59-5,90366-07-7)

Guidance literature:

C₁₁H₁₅N₅O₄; With palladium on carbon; hydrogen; In water; at 20 ℃; for 80h; under 4500.45 Torr; Large scale;

With hydrogenchloride; In water; Reagent/catalyst; Solvent; Temperature; Large scale;

Reference yield: 15.8%

biopterin (22150-76-1) → (6S)-tetrahydrobiopterin dihydrochloride + Sapropterin dihydrochloride (69056-38-8,69056-39-9,71074-53-8,83023-72-7,83709-59-5,90366-07-7)

Guidance literature:

biopterin; With sodium tetrahydroborate; In ethanol;

With hydrogenchloride;

Reference yield:

biopterin (22150-76-1) → Sapropterin dihydrochloride (69056-38-8,69056-39-9,71074-53-8,83023-72-7,83709-59-5,90366-07-7)

Guidance literature:

With hydrogenchloride; platinum(IV) oxide; tetramethyl ammoniumhydroxide; water; at 25 ℃; for 8h; under 9000.9 Torr; pH=Ca. 11.5; Reagent/catalyst; Pressure; Inert atmosphere;

upstream raw materials:

biopterin

(3S,4S)-1-amino-3,4-dihydroxy-2-pentanone

Downstream raw materials:

(R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-4-oxo-4,6,7,8-tetrahydro-3H-pteridine-5-carboxylic acid benzyl ester

p-quinonoid (6R)-dihydrobiopterin hydrochloride

Refernces

• 1、 -. "METHOD FOR SYNTHESIZING SAPROPTERIN DIHYDROCHLORIDE". . . Retrieved 2015/03/03.
• 2、 -. "METHOD FOR SYNTHESIZING SAPROPTERIN DIHYDROCHLORIDE". . . Retrieved 2015/04/22.