5-amino-6-(D-ribitylamino)uracil

Base Information

• Chemical Name: 5-amino-6-(D-ribitylamino)uracil
• CAS No.: 17014-74-3
• Molecular Formula: C9H16 N4 O6
• Molecular Weight: 276.249
• DSSTox Substance ID: DTXSID60937742
• Nikkaji Number: J642.641G
• Wikidata: Q27098306
• Metabolomics Workbench ID: 50314
• Mol file: 17014-74-3.mol

Synonyms:5-amino-2,6-dioxo-4-ribitylaminopyrimidine;5-amino-6-ribitylamino-2,4-(1H,3H)pyrimidinedione;5-ARPD;A-4-RAP

Chemical Property of 5-amino-6-(D-ribitylamino)uracil

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 11.60±0.10(Predicted)
• Flash Point: °C
• PSA: 184.69000
• Density: 1.67g/cm³
• LogP: -3.21350
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 276.10698424
• Heavy Atom Count: 19
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(C(CO)O)O)O)NC1=C(C(=O)NC(=O)N1)N
• Isomeric SMILES: C([C@@H]([C@@H]([C@@H](CO)O)O)O)NC1=C(C(=O)NC(=O)N1)N

Technology Process of 5-amino-6-(D-ribitylamino)uracil

There total 11 articles about 5-amino-6-(D-ribitylamino)uracil 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: 98.0%

5-nitroso-6-D-(ribitylamino)pyrimidine-2,4(1H,3H)-dione (75599-13-2) → 5-amino-6-(D-ribitylamino)uracil (14036-89-6,17014-74-3)

Guidance literature:

With sodium dithionite;

DOI:10.1371/journal.pone.0191837

Reference yield:

6,7-dimethyl-8-ribityllumazine (2535-20-8,5118-16-1) → 5-amino-6-(D-ribitylamino)uracil (14036-89-6,17014-74-3) + riboflavin (83-88-5,42880-33-1)

Guidance literature:

With ethylenediaminetetraacetic acid; riboflavin synthase from Escherichia coli; 5-(4-phosphonobutyryl)amino-6-D-ribitylaminouracil; In phosphate buffer; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1021/jo020144r

Reference yield:

5-nitro-6-(((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)amino)pyrimidine-2,4(1H,3H)-dione (52850-67-6,52850-68-7,52918-38-4,52918-39-5) → 5-amino-6-(D-ribitylamino)uracil (14036-89-6,17014-74-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; Ambient temperature;

upstream raw materials:

5-nitro-6-(((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)amino)pyrimidine-2,4(1H,3H)-dione

6,7-dimethyl-8-ribityllumazine

5-nitroso-6-D-(ribitylamino)pyrimidine-2,4(1H,3H)-dione

D-Ribamin

Downstream raw materials:

6-benzyl-7-methyl-8-D-ribitylpteridine-2,4(3H,8H)-dione

6,7-diphenyl-8-D-ribitylpteridine-2,4(3H,8H)-dione

6-carboxyethyl-7-oxo-8-D-ribityl-lumazine

5-(4-dibenzylphosphonobutyryl)amino-6-D-ribitylaminouracil

Refernces

• 1、 Anderson, Regan J.,Bilbrough, Timothy S.,Cerundolo, Vincenzo,Chan, Susanna T. S.,Gasser, Olivier,Gonzalez-Lopez, Claudia,Hermans, Ian F.,Lange, Joshua,Marshall, Andrew J.,Painter, Gavin F.,Salio, Mariolina. "The Chemical Synthesis, Stability, and Activity of MAIT Cell Prodrug Agonists That Access MR1 in Recycling Endosomes". . . Retrieved 2020/02/04.
• 2、 -. "MAIT CELL AGONISTS". Page/Page column 78-79. . Retrieved 2019/04/16.