Russupteridine IV

Base Information

• Chemical Name: Russupteridine IV
• CAS No.: 2535-20-8
• Molecular Formula: C13H18 N4 O6
• Molecular Weight: 326.309
• UNII: O1DSD0WC7M
• DSSTox Substance ID: DTXSID90199199
• Nikkaji Number: J643.571H
• Wikipedia: 6,7-Dimethyl-8-ribityllumazine
• Wikidata: Q4641523
• Metabolomics Workbench ID: 50971
• Mol file: 2535-20-8.mol

Synonyms:Lumazine,6,7-dimethyl-8-(D-ribo-2,3,4,5-tetrahydroxypentyl)- (6CI,7CI,8CI); 2,4(1H,3H)-Pteridinedione,6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-, [2S-(2R*,3R*,4S*)]-;6,7-Dimethyl-8-(1'-D-ribityl)lumazine; 6,7-Dimethyl-8-(D-ribityl)lumazine;6,7-Dimethyl-8-ribityllumazine; 6,7-Dimethylribityllumazine;6,7-Dimethylribolumazine; Russupteridine IV

Chemical Property of Russupteridine IV

Chemical Property:

• Melting Point: 272-274 °C (decomp)
• PKA: 9.39±0.70(Predicted)
• PSA: 161.56000
• Density: 1.70±0.1 g/cm3(Predicted)
• LogP: -2.82840
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 326.12263431
• Heavy Atom Count: 23
• Complexity: 626

Purity/Quality:

99%, ^*data from raw suppliers

6,7-Dimethylribityl Lumazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N(C2=NC(=O)NC(=O)C2=N1)CC(C(C(CO)O)O)O)C
• Isomeric SMILES: CC1=C(N(C2=NC(=O)NC(=O)C2=N1)C[C@@H]([C@@H]([C@@H](CO)O)O)O)C
• Description: 6,7-dimethyl-8-Ribityllumazine (DMRL) is a natural chromophore of lumazine protein (LumP), a fluorescent accessory protein that induces a blue shift (495 to 475 nm) in luciferase emission wavelengths in bioluminescent Photobacterium. DMRL binds noncovalently to both the N- and C-terminal domains of LumP. It is also a biosynthetic precursor of riboflavin and substrate of riboflavin synthase.
• Uses: 6,7-Dimethyl-8-ribityllumazine serves as fluorophore in Lumazine (L473800) proteins (LumP) of luminescent bacteria.

Technology Process of Russupteridine IV

There total 16 articles about Russupteridine IV 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: 39.0%

5-amino-6-(D-ribitylamino)uracil (14036-89-6,17014-74-3) + dimethylglyoxal (431-03-8) → C13H20N4O6 + C13H20N4O6 + 6,7-dimethyl-8-ribityllumazine (2535-20-8,5118-16-1)

Guidance literature:

at 20 - 80 ℃; for 3h; Overall yield = 65 percent;

DOI:10.1039/c9ob01436e

Reference yield: 2.5%

D-Glucose (2280-44-6) → 6,7-dimethyl-8-ribityllumazine (2535-20-8,5118-16-1)

Guidance literature:

With Escherichia coli strain; isopropyl β-D-thiogalactopyranoside; In water; at 37 ℃; for 15h; Enzymatic reaction;

DOI:10.1021/jo0493222

Reference yield:

5-amino-6-(D-ribitylamino)uracil (14036-89-6,17014-74-3) + 3,4-dihydroxy-2-butanone 4-phosphate (114155-98-5,130971-02-7) → 6,7-dimethyl-8-ribityllumazine (2535-20-8,5118-16-1)

Guidance literature:

With Tris-HCl buffer; lumazine synthase from Magnaporthe grisea; diothiothreitol; at 25 ℃; pH=7.5; Further Variations:; pH-values; Reagents; Temperatures; Enzyme kinetics; Activation energy;

DOI:10.1006/bioo.2000.1163

upstream raw materials:

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

3-hydroxy-2-butanon

dimethylglyoxal

3,4-dihydroxy-2-butanone 4-phosphate

Downstream raw materials:

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

riboflavin

6-Methyl-7-oxo-N(8)-(D-ribityl)-7,8-dihydro-Lumazin

Refernces

• 1、 Beach,Plaut. "-". . p. 2913,2914, 2915. Retrieved 1970.
• 2、 Zheng, Ya-Jun,Viitanen, Paul V.,Jordan, Douglas B.. "Rate limitations in the lumazine synthase mechanism". . p. 89 - 97. Retrieved 2000.
• 3、 Braganza, Chriselle D.,Shibata, Kensuke,Fujiwara, Aisa,Motozono, Chihiro,Sonoda, Koh-Hei,Yamasaki, Sho,Stocker, Bridget L.,Timmer, Mattie S. M.. "The effect of MR1 ligand glyco-analogues on mucosal-associated invariant T (MAIT) cell activation". . p. 8992 - 9000. Retrieved 2019/10/28.
• 4、 Talukdar, Arindam,Morgunova, Ekaterina,Duan, Jianxin,Meining, Winfried,Foloppe, Nicolas,Nilsson, Lennart,Bacher, Adelbert,Illarionov, Boris,Fischer, Markus,Ladenstein, Rudolf,Cushman, Mark. "Virtual screening, selection and development of a benzindolone structural scaffold for inhibition of lumazine synthase". experimental part. p. 3518 - 3534. Retrieved 2010/08/05.