62989-33-7

Basic information

• Product Name: (6R,S)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE
• Synonyms: 4(1H)-PTERIDINONE, 2-AMINO-6-[(1R,2S)-1,2-DIHYDROXYPROPYL]-5,6,7,8-TETRAHYDRO-, (6R)-;(6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE;(6R,S)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE;(6R,S)-BH4 2HCL;sapropterin;2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-Pteridinone;(6R)-5,6,7,8-Tetrahydrobiopterin;(6R)-L-erythro-5,6,7,8-Tetrahydrobiopterin
• CAS NO: 62989-33-7
• Molecular Formula: C₉H₁₅N₅O₃
• Molecular Weight: 314.17
• EINECS: 1533716-785-6
• Mol File: 62989-33-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 506.6 °C at 760 mmHg
• Flash Point: 260.2 °C
• Appearance: /
• Density: 1.89g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.822
• Storage Temp.: −20°C
• PKA: 5.05(at 25℃)
• CAS DataBase Reference: (6R,S)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,S)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE(62989-33-7)
• EPA Substance Registry System: (6R,S)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE(62989-33-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: UO3516500
• Hazardous Substances Data: 62989-33-7(Hazardous Substances Data)

Usage

Uses

Treatment of mild-to-moderate phenylketonuria (PKU).

InChI:InChI=1/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4?,6-/m0/s1

Synthetic route

biopterin (22150-76-1) → (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7) + (6S)-tetrahydrobiopterin (62961-57-3)

Conditions	Yield
With hydrogen; platinum(IV) oxide In water at 15℃; for 18h; pH=11.8;	A 79% B n/a
With potassium hydroxide; dipotassium hydrogenphosphate; hydrogen; platinum(IV) oxide In water at 20℃; under 735.5 Torr; for 4.5h; pH 11.4;	A 67% B n/a
With potassium hydroxide; dipotassium hydrogenphosphate; hydrogen; platinum(IV) oxide In water at 20℃; under 735.5 Torr; Product distribution; the influence of pH;

p-quinonoid (6R)-dihydrobiopterin (79647-29-3) → 7,8-dihydro-L-biopterin (6779-87-9) + (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7) + biopterin (22150-76-1)

Conditions	Yield
pH=7;
In water Product distribution; pH 3.5 ; half life time; other pH; also with NADPH;

(6R)-2-acetamido-5,8-diacetyl-6-[(1R,2S)-1,2-bis(acetyloxy)propyl]-5,6,7,8-tetrahydropteridin-4(3H)-one → (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7)

Conditions	Yield
With hydrogenchloride In water at 22℃;

6-((1R,2R)-1,2-dihydroxy-3-phenylthiopropyl)-2-[(methylethyl)amino]-3-hydropteridin-4-one → (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7)

Conditions	Yield
With BH4; hydrogen; nickel In ethanol at 60℃; under 3750.38 Torr; for 17h;

dioxomolybdenum(VI) dichloride (13637-68-8) + (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7) → trichloro{(1'R,2'S,6R)-2-iminio-6-(1',2'-dihydroxypropyl)-3,6,7,8-tetrahydropteridin-4(3H)-one-O(4),N(5)}oxomolybdenum(IV)*MeOH

Conditions	Yield
In methanol byproducts: H2O, HCl; under protective gas, toluene/cyclohexane added, allowed to stand at 4°C overnight; filtrated, dried in high vacuum, elem. anal.;	97.1%

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7) → 7,8-dihydrobiopterin (1262750-77-5)

Conditions	Yield
With oxygen In aq. phosphate buffer at 25℃; for 1h; pH=7.2; Kinetics;	34.6%

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7) → 7,8-dihydrobiopterin (1262750-77-5) + D-erythro-biopterin (13039-62-8)

Conditions	Yield
With oxygen In aq. acetate buffer at 25℃; for 1h; pH=7.2;	A 15.7% B 24.2%

di-tert-butyl dicarbonate (24424-99-5) + (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7) → [6R(1R,2S)]-2-t-butoxycarbonylamino-4-t-butoxycarbonyloxy-5,8-di-t-butoxycarbonyl-6-(1,2 dihydroxypropyl)-5,6,7,8-tetrahydropterdin (908119-99-3)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20 - 60℃; for 20h;

Upstream product

• 22150-76-1 biopterin 
• 79647-29-3 p-quinonoid (6R)-dihydrobiopterin 

Downstream Products

• 1262750-77-5 7,8-dihydrobiopterin 
• 13039-62-8 D-erythro-biopterin 

Relevant articles and documents

The configuration at C(6) of natural 5,6,7,8-tetrahydro-L-biopterin and of its pentaacetate

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Quinonoid Dihydrobiopterin, an Important Metabolic Intermediate of Biopterin Cofactor in the Aromatic Hydroxylation of Amino Acids

p-Quinonoid (6R)-dihydrobiopterin hydrochloride was synthesized from (6R)-5,6,7,8-tetrahydrobiopterin dihydrochloride by hydrogenperoxide in the presence of potassium iodide.Several characters of quinonoid dihydrobiopterin were examined.

HIGHLY STEREOSELECTIVE PROCEDURE FOR (6R)-TETRAHYDROBIOPTERIN COFACTOR

(6R)-Tetrahydrobiopterin cofactor for aromatic amino acid hydroxylases was synthesized stereoselectively by catalytic hydrogenation of biopterin over platinum oxide at pH 11.4 and subsequent crystallization from hydrochloric acid and ethanol.