17094-01-8

Basic information

• Product Name: L-SEPIAPTERIN
• Synonyms: (S)-2-aMino-6-(2-hydroxypropanoyl)-7,8-dihydropteridin-4(1H)-one;(S)-2-AMino-6-(2-hydroxypropanoyl)-7,8-dihydropteridin-4(3H)-one;Sepiapterin solid;S(-)-2-AMINO-7,8-DIHYDRO-6-(2-HYDROXY-1-OXOPROPYL)-4(1H)-PTERIDINONE;SEPIAPTERIN;L-SEPIAPTERIN;L-SEPIAPTERIN DIHYDRATE;2-AMINO-7,8-DIHYDRO-6-(2S-HYDROXY-1-OXOPROPYL)-4(1H)-PTERIDINONE
• CAS NO: 17094-01-8
• Molecular Formula: C₉H₁₁N₅O₃
• Molecular Weight: 237.22
• Mol File: 17094-01-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 448.1 °C at 760 mmHg
• Flash Point: 224.8 °C
• Appearance: yellow/solid
• Density: 1.86 g/cm³
• Vapor Pressure: 6.54E-10mmHg at 25°C
• Refractive Index: 1.821
• Storage Temp.: −20°C
• Solubility: DMSO: 27 mg/mL
• PKA: 12.33±0.20(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: L-SEPIAPTERIN(CAS DataBase Reference)
• NIST Chemistry Reference: L-SEPIAPTERIN(17094-01-8)
• EPA Substance Registry System: L-SEPIAPTERIN(17094-01-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 17094-01-8(Hazardous Substances Data)

Usage

Description

L-SEPIAPTERIN, a pteridine derivative, is a stable precursor of tetrahydrobiopterin (BH4). It is a yellow pigment found in the sepia mutant of Drosophila melanogaster and lemon Bombyx mori mutant (silkworm). As a yellow to orange powder, it serves as a substrate for BH4 synthesis via the pterin salvage pathway and has the ability to inhibit rat liver GTP cyclohydrolase.
Used in Pharmaceutical Industry:
L-SEPIAPTERIN is used as a precursor for BH4 synthesis, playing a crucial role in the pterin salvage pathway. Its ability to inhibit rat liver GTP cyclohydrolase with an IC50 value of approximately 25 μM makes it a valuable compound in the development of treatments for certain diseases and conditions.
Used in Diabetes Research and Treatment:
In the field of diabetes research and treatment, L-SEPIAPTERIN is used to improve endothelial dysfunction in subjects with Type I Diabetes, such as db/db mice, by decreasing oxidative stress. This application highlights its potential in managing and studying the complications associated with diabetes.
Used in DNA Research:
L-SEPIAPTERIN can also be used in DNA research to induce sequence-specific photolesions in double-stranded DNA. This property makes it a useful tool for studying DNA structure, function, and repair mechanisms, contributing to a broader understanding of genetic processes and potential therapeutic targets.
Used as a Research Tool:
Furthermore, L-SEPIAPTERIN can be used as a research tool to circumvent the inhibition of pterin biosynthesis by 2,4-diamino-6-hydroxy pyrimidine. This application is beneficial for scientists studying the effects of pterin pathway inhibition and the role of L-SEPIAPTERIN in various biological processes.

Biochem/physiol Actions

Cofactor of nitric oxide synthase; intracellularly converted to tetrahydro-biopterin leading to the stimulation of nitric oxide.

InChI:InChI=1/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1

Synthetic route

2-amino-6-(2S-2-hydroxypropionyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one dihydrochloride → sepiapterin (17094-01-8)

Conditions	Yield
With dihydrogen peroxide In ethanol; water at -10℃; for 2h; Reagent/catalyst; Temperature; Solvent;	89%

1-[4-tert-butoxycarbonyloxy-2-(N,N-di-tert-butoxycarbonyl)amino-7,8-dihydropteridin-6-yl]-2S-2-(tert-butyldimethylsilanyloxy)propan-1-one → sepiapterin (17094-01-8)

Conditions	Yield
Stage #1: 1-[4-tert-butoxycarbonyloxy-2-(N,N-di-tert-butoxycarbonyl)amino-7,8-dihydropteridin-6-yl]-2S-2-(tert-butyldimethylsilanyloxy)propan-1-one With hydrogenchloride In water; acetonitrile at 50℃; for 3h; Stage #2: With sodium hydroxide In water; acetonitrile pH=7;	88%

1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one → sepiapterin (17094-01-8)

Conditions	Yield
Stage #1: 1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one With hydrogenchloride; ascorbic acid In methanol; water at 50℃; for 6h; Darkness; Stage #2: With ammonia In methanol; water pH=7;	86%

S-lactoylpterin → sepiapterin (17094-01-8)

Conditions	Yield
With Pd/C (Ph2S); hydrogen; triethylamine In methanol; water at 40℃; for 3h; Reagent/catalyst; Solvent; Temperature;	59%

1-(2-amino-4-cyclohexyloxypteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one → sepiapterin (17094-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / methanol; water / 3 h / 50 °C 1.2: pH 7 2.1: hydrogen; Pd/C (Ph2S); triethylamine / methanol; water / 3 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen; potassium carbonate; palladium 10% on activated carbon / ethyl acetate / 3 h / 50 °C 2.1: hydrogenchloride / water / Heating 2.2: pH 6 - 7 View Scheme

1-(2-amino-4-cyclohexyloxypteridin-6-yl)-1R,2S-1-hydroxy-2-(methoxymethoxy)propan (1104608-07-2) → sepiapterin (17094-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 1 h / 60 °C / Inert atmosphere; Molecular sieve 2.1: hydrogenchloride / methanol; water / 3 h / 50 °C 2.2: pH 7 3.1: hydrogen; Pd/C (Ph2S); triethylamine / methanol; water / 3 h / 40 °C View Scheme
Multi-step reaction with 3 steps 1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 1 h / 60 °C / Inert atmosphere; Molecular sieve 2.1: hydrogen; potassium carbonate; palladium 10% on activated carbon / ethyl acetate / 3 h / 50 °C 3.1: hydrogenchloride / water / Heating 3.2: pH 6 - 7 View Scheme

1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one → sepiapterin (17094-01-8)

Conditions	Yield
Stage #1: 1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one With hydrogenchloride In water Heating; Stage #2: With sodium hydroxide In water pH=6 - 7;

1-(2-amino-4-cyclohexyloxypteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one → sepiapterin (17094-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; ascorbic acid; sodium dithionite / methanol; water / 1 h / 20 °C 2.1: hydrogenchloride; ascorbic acid / methanol; water / 6 h / 50 °C / Darkness 2.2: pH 7 View Scheme

sepiapterin (17094-01-8) → S-sepiapterin hydrochloride

Conditions	Yield
With hydrogenchloride In ethanol; water at 0℃; for 0.5h;	91%

Upstream product

• 1104608-07-2 1-(2-amino-4-cyclohexyloxypteridin-6-yl)-1R,2S-1-hydroxy-2-(methoxymethoxy)propan 

Downstream Products

• 490-79-9 2,5-dihydroxybenzoic acid. 

Relevant articles and documents

METHOD FOR PRODUCING SEPIAPTERIN AND TETRAHYDROLACTOYLPTERIN

To provide a method for producing sepiapterin, lactoylpterin or tetrahydrolactoylpterin. Sepiapterin, lactoylpterin and tetrahydrolactoylpterin are produced at high yield through the following reaction scheme.