D-(+)-NEOPTERIN

Base Information

• Chemical Name: D-(+)-NEOPTERIN
• CAS No.: 2009-64-5
• Molecular Formula: C9H11N5O4
• Molecular Weight: 253.217
• Hs Code.: 29335990
• Mol file: 2009-64-5.mol

Synonyms:1,2,3-Propanetriol,1-(2-amino-4-hydroxy-6-pteridinyl)-, D-erythro- (8CI);D-(+)-Neopterin;D-Neopterin;2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]pteridin-4(1H)-one;6-(D-Erythro-1,2,3-Trihydroxypropyl)pterin;

Chemical Property of D-(+)-NEOPTERIN

Chemical Property:

• Appearance/Colour: Off-white to yellow solid
• Melting Point: >232°C (dec.)
• Refractive Index: 1.86
• Boiling Point: 697.7 °C at 760 mmHg
• PKA: 12.60±0.20(Predicted)
• Flash Point: 375.7 °C
• PSA: 158.50000
• Density: 2.02 g/cm³
• LogP: -1.32460
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-Neopterin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Neopterin is a pyrazino-pyrimidine compound derived from GTP that represents an intermediate product in the synthetic pathway of biopterin and is an essential cofactor in neurotransmitter synthesis. Neopterin is released from macrophages upon immune stimulation with interferon-γ from activated T cells. It is routinely used as a biochemical tool to screen for and monitor the progression of certain diseases accompanied by hyperimmune stimulation.
• Uses: Precursor in the biosynthesis of Biopterin. First isolated from the pupae of bees. D-(+)-Neopterin has been used as a NADPH oxidase inhibitor while assessing the ability of NADPH oxidases in breast cancer cells to produce reactive oxygen species (ROS). [NADPH= nicotinamide adenine dinucleotide phosphate]

Technology Process of D-(+)-NEOPTERIN

There total 7 articles about D-(+)-NEOPTERIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + D-arabinose-phenylhydrazone (28767-74-0) → Neopterin (2009-64-5)

Guidance literature:

2,5,6-triamino-3,4-dihydro-4-pyrimidinone; D-arabinose-phenylhydrazone; With sulfuric acid; In methanol; water; for 2h; Reflux;

at 20 ℃; for 2h;

DOI:10.3987/COM-16-S(S)32

Reference yield: 62.0%

4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-2-(methylthio)pteridine (76212-27-6) → Neopterin (2009-64-5)

Guidance literature:

With ammonium hydroxide; ammonium acetate; for 4h; Heating;

DOI:10.1246/bcsj.53.2344

Reference yield: 2.0%

tetrahydro-5,6,7,8-D-neopterine-(6R,S) → desoxy-2'-neopterine + sepiapterine + desoxy-2'-hydroxy-3'-sepiapterine + Neopterin (2009-64-5)

Guidance literature:

With air; sodium acetate; In water; Further byproducts given; at pH 4.5, in the dark;

DOI:10.1002/hlca.19810640418

upstream raw materials:

D-ribose

4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-2-(methylthio)pteridine

D-arabinose-phenylhydrazone

2,5,6-triamino-3,4-dihydro-4-pyrimidinone

Downstream raw materials:

dihydro-7,8-D-neopterine

6-hydroxymethylpterin

Refernces

• 1、 Sakurai,Goto. "Neopterin: isolation from human urine.". . p. 142 - 145. Retrieved 1967.
• 2、 Antoulas, Simeon,Viscontini, Max. "Synthesis of 5,6,7,8-Tetrahdro-D-neopterine tripolyphosphate. Attempt to Interpret the Biosynthesis of L-Sepiapterine". . p. 1134 - 1139. Retrieved 2007/10/02.