6-Biopterin CAS#: 22150-76-1; 凯望编码 (ChemWhat Code): 239571

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名6-Biopterin
IUPAC Name2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3H-pteridin-4-one
分子结构6-Biopterin-CAS-22150-76-1
CAS编号 22150-76-1
EINECS Number244-807-8
MDL NumberMFCD00036787
Beilstein Registry Number87860
别名6-Biopterin
L-Biopterin
22150-76-1
biopterin
L-Erythro-Biopterin
(-)-Biopterin
Pterin H B2
E54CTM794Y
2-amino-6-((1R,2S)-1,2-dihydroxypropyl)pteridin-4(1H)-one
4(1H)-Pteridinone, 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-
NSC-339699
2-amino-6-((1R,2S)-1,2-dihydroxypropyl)pteridin-4(3H)-one
NSC 339699
UNII-E54CTM794Y
Oxygenase, tyrosine 3-mono-
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(3H)-one
MFCD00036787
4(1H)-PTERIDINONE, 2-AMINO-6-((1R,2S)-1,2-DIHYDROXYPROPYL)-
L-erythro biopterin
EINECS 244-807-8
BIOPTERIN [MI]
4(1H)-Pteridinone, 2-amino-6-(1,2-dihydroxypropyl)-, (S-(R,S))-
(1’R,1’S) Biopterin
6-Biopterin, >=97%
SCHEMBL258466
SCHEMBL18662632
CHEBI:63931
DTXSID30912041
(L-erythro)-2-Amino-6-(1,2-dihydroxypropyl)-4(3H)-pteridinon
BCP04171
s5577
AKOS025312532
AKOS028109358
AKOS030254292
CCG-266851
CS-6962
9036-22-0
AC-28999
AS-70364
6-(L-erythro-1,2-dihydroxypropyl)-pterin
HY-102015
B6302
EN300-7365623
Q408256
W-201921
Z3245415986
2-amino-6-(L-erythro-1,2-dihydroxypropyl)-4(3H)-Pteridinone
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3H-pteridin-4-one
(S-(R,S))-2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one
[S-(R,S)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-Pteridinone
4(3H)-Pteridinone, 2-amino-6-(L-erythro-1,2-dihydroxypropyl)-
(1R,2S)-1-(2-AMINO-4-HYDROXYPTERIDIN-6-YL)PROPANE-1,2-DIOL
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3,4-dihydropteridin-4-one
分子式C9H11N5O3
分子量237.22
InChIInChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1
InChI KeyLHQIJBMDNUYRAM-DZSWIPIPSA-N
Isomeric SMILESC[C@@H]([C@@H](C1=CN=C2C(=N1)C(=O)NC(=N2)N)O)O
Patent Information
Patent IDTitlePublication Date
CN112390800Preparation method of L-erythro biopterin compound2021

Physical Data

AppearanceYellow Solid
Melting Point, °C Solvent (Melting Point)
300aq. NH3, formic acid
H2O

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts1Htrifluoroacetic acid-d1
Chemical shifts13Cdioxane, various solvent(s)
Chemical shifts1Hvarious solvent(s)
Spectrum1Hdimethylsulfoxide-d6
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
Bandspotassium bnujol
BandsKBr
Intensity of IR bands
BandsKBr
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
2606527
Spectrumwater
water, hydrogenchloride3228000
SpectrumH2O200 – 450 nm

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Sapropterin Impurity C CAS 22150-76-1
Route of Synthesis (ROS) of Sapropterin Impurity C CAS 22150-76-1
ConditionsYield
Stage #1: biopterin With platinum(IV) oxide; hydrogen; tetraethylammonium hydroxide In water at 20℃; under 15001.5 Torr; for 24h; pH=12;
Stage #2: With hydrogenchloride In water Reagent/catalyst;

Experimental Procedure

7-8 Example 8 Synthesis of sapropterin hydrochloride 2
DL-5 (20 g, 0.084 mol), water (200 mL) was added to the reaction vessel.Add 25% aqueous solution of tetraethylammonium hydroxide,The pH was adjusted to 12 and DL-5 was substantially completely dissolved.The mixture was transferred to a 2 L hydrogenation reactor, and platinum dioxide (2.0 g) was added thereto. After replacing three times with hydrogen, the mixture was hydrogenated to 2 MPa, and reacted at room temperature for 24 hours. The reaction was monitored by HPLC until the reaction was completed.The catalyst was removed by filtration, the filtrate was collected, concentrated hydrochloric acid was added, the mixture was adjusted to pH 1 and the solvent was evaporated to dryness, and ethyl alcohol (2000 mL) was added, and the mixture was stirred for 1 hour, and the filtrate was collected and dried to give a brown-brown oil (22 g).Add 66 mL of concentrated HCl (10N), heat to complete dissolution, add ethanol (220 mL), precipitate solids, filter, rinse with ethanol, collect solids, and dry.White crystals of sapropterin hydrochloride 17.9g,The yield was 88.3% and the ee value was 99%.The HPLC diagram of the final product of sapropterin hydrochloride is shown in Figure 2 of the specification.		88.3%

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement CodesP261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

HS Code
StorageStore at 2~8 °C for long time, sealed and away from light.
Shelf Life3 years
Market Price
Druglikeness
Lipinski rules component
分子量237.218
logP-2.183
HBA8
HBD4
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)3133.72
Rotatable Bond (RotB)2
Matching Veber Rules2
Use Pattern
6-Biopterin CAS#: 22150-76-1 is used in pharmaceutical intermediates.

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