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Sapropterin

  • Name Sapropterin
  • EINECS636-312-4
  • CAS No. 62989-33-7
  • Density1.89g/cm3
  • PSA136.29000
  • LogP-0.84300
  • SolubilityN/A
  • Melting PointN/A
  • FormulaC9H15N5O3
  • Boiling Point506.6 °C at 760 mmHg
  • Molecular Weight241.25
  • Flash Point260.2 °C
  • Transport InformationN/A
  • AppearanceN/A
  • Safety
  • Risk Codes22
  • Molecular Structure
    Molecular Structure of 62989-33-7 ((6R,S)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE)
  • Hazard SymbolsXn
  • SynonymsXn
  • Article Data5

Sapropterin Synthetic route

22150-76-1

biopterin

A

62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

B

62961-57-3

(6S)-tetrahydrobiopterin

Conditions
ConditionsYield
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;
79647-29-3

p-quinonoid (6R)-dihydrobiopterin

A

6779-87-9

7,8-dihydro-L-biopterin

B

62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

C

22150-76-1

biopterin

Conditions
ConditionsYield
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

62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 22℃;

6-((1R,2R)-1,2-dihydroxy-3-phenylthiopropyl)-2-[(methylethyl)amino]-3-hydropteridin-4-one

62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

Conditions
ConditionsYield
With BH4; hydrogen; nickel In ethanol at 60℃; under 3750.38 Torr; for 17h;
13637-68-8

dioxomolybdenum(VI) dichloride

62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

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
ConditionsYield
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%
62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

1262750-77-5

7,8-dihydrobiopterin

Conditions
ConditionsYield
With oxygen In aq. phosphate buffer at 25℃; for 1h; pH=7.2; Kinetics;34.6%
62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

A

1262750-77-5

7,8-dihydrobiopterin

B

13039-62-8

D-erythro-biopterin

Conditions
ConditionsYield
With oxygen In aq. acetate buffer at 25℃; for 1h; pH=7.2;A 15.7%
B 24.2%
24424-99-5

di-tert-butyl dicarbonate

62989-33-7

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride

908119-99-3

[6R(1R,2S)]-2-t-butoxycarbonylamino-4-t-butoxycarbonyloxy-5,8-di-t-butoxycarbonyl-6-(1,2 dihydroxypropyl)-5,6,7,8-tetrahydropterdin

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

Sapropterin Chemical Properties

Molecular Structure of Sapropterin (CAS NO.62989-33-7):

IUPAC Name: (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one 
Empirical Formula: C9H15N5O3
Molecular Weight: 241.2471
H bond acceptors: 8
H bond donors: 7
Freely Rotating Bonds: 4
Polar Surface Area: 60.85 Å2
Index of Refraction: 1.821
Molar Refractivity: 55.42 cm3
Molar Volume: 127.1 cm3
Surface Tension: 86.7 dyne/cm
Density: 1.89 g/cm3
Flash Point: 260.2 °C
Enthalpy of Vaporization: 89.4 kJ/mol
Boiling Point: 506.6 °C at 760 mmHg
Vapour Pressure: 2.2E-12 mmHg at 25°C
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
Smiles
n1c(N)[nH]c2NC[C@@H](Nc2c1=O)[C@H]([C@H](C)O)O

Sapropterin Specification

  Sapropterin , with CAS number of 62989-33-7, can be called 4(1H)-Pteridinone,2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-, [6R-[6R*(1R*,2S*)]]- ; (6R)-5,6,7,8-Tetrahydro-L-biopterin ; (6R)-5,6,7,8-Tetrahydrobiopterin ; (6R)-L-erythro-5,6,7,8-Tetrahydrobiopterin ; (6R)-L-erythro-Tetrahydrobiopterin ; 6b-5,6,7,8-Tetrahydro-L-biopterin ; (-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8- ; 6R-5,6,7,8-Tetrahydrobiopterin ; 6R-L-5,6,7,8-Tetrahydrobiopterin ; Kuvan .

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