6-Biopterin CAS#: 22150-76-1; ChemWhat Code: 239571
Identification
| Product Name | 6-Biopterin |
| IUPAC Name | 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3H-pteridin-4-one |
| Molecular Structure |  |
| CAS Registry Number | 22150-76-1 |
| EINECS Number | 244-807-8 |
| MDL Number | MFCD00036787 |
| Beilstein Registry Number | 87860 |
| Synonyms | 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 |
| Molecular Formula | C9H11N5O3 |
| Molecular Weight | 237.22 |
| InChI | InChI=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 Key | LHQIJBMDNUYRAM-DZSWIPIPSA-N |
| Isomeric SMILES | C[C@@H]([C@@H](C1=CN=C2C(=N1)C(=O)NC(=N2)N)O)O |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| CN112390800 | Preparation method of L-erythro biopterin compound | 2021 |
Physical Data
| Appearance | Yellow Solid |
| Melting Point, °C | Solvent (Melting Point) |
| 300 | aq. NH3, formic acid |
| H2O |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) |
| Chemical shifts | 1H | trifluoroacetic acid-d1 |
| Chemical shifts | 13C | dioxane, various solvent(s) |
| Chemical shifts | 1H | various solvent(s) |
| Spectrum | 1H | dimethylsulfoxide-d6 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) |
| Bands | potassium bnujol |
| Bands | KBr |
| Intensity of IR bands | |
| Bands | KBr |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Comment (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm | Ext./Abs. Coefficient, l·mol-1cm-1 |
| 260 | 6527 | |||
| Spectrum | water | |||
| water, hydrogenchloride | 322 | 8000 | ||
| Spectrum | H2O | 200 – 450 nm |
Route of Synthesis (ROS)
| Conditions | Yield |
| 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) |  |
| Signal | Warning |
| GHS Hazard Statements | H315 (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 Codes | P261, 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 | |
| Storage | Store at 2~8 °C for long time, sealed and away from light. |
| Shelf Life | 3 years |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 237.218 |
| logP | -2.183 |
| HBA | 8 |
| HBD | 4 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 3133.72 |
| Rotatable Bond (RotB) | 2 |
| Matching Veber Rules | 2 |
| Use Pattern |
| 6-Biopterin CAS#: 22150-76-1 is used in pharmaceutical intermediates. |
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| Caming Pharmaceutical Limited | http://www.caming.com/ |
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Other Suppliers | |
| Watson International Limited | Visit Watson Official Website |
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