[[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate

Base Information

• Chemical Name: [[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate
• CAS No.: 85-61-0
• Molecular Formula: C21H36N7O16P3S
• Molecular Weight: 767.541
• Hs Code.: 2933299090
• European Community (EC) Number: 201-619-0
• Mol file: 85-61-0.mol

Synonyms:[[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate;85-61-0

Chemical Property of [[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate

Chemical Property:

• Appearance/Colour: yellowish lyophilisate
• Melting Point: -5oC
• Refractive Index: 1.736
• Boiling Point: 146 - 147
• PKA: 9.6 (thiol); pK 6.4 (secondary phosphate); pK 4.0 (adenine NH3+)
• PSA: 414.79000
• Density: 1.962 g/cm³
• LogP: -0.30230
• Storage Temp.: −20°C
• XLogP3: -5.8
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 21
• Rotatable Bond Count: 18
• Exact Mass: 767.11521025
• Heavy Atom Count: 48
• Complexity: 1270

Purity/Quality:

99%, ^*data from raw suppliers

CoenzymeA,FreeAcid,Hydrate(CoA) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Chemical Classes: Biological Agents -> Other Biomolecules
• Canonical SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCS)O
• Isomeric SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCS)O
• Description: Coenzyme A (CoA) is an essential cofactor functioning as an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. About 4% of cellular enzymes utilize CoA as a substrate. It is synthesized from pantothenic acid in a 5-step process that requires ATP. The pantothenate kinase step of the CoA biosynthetic pathway has been identified as a target for the development of antibacterial compounds.
• Uses: A hydrated form of Coenzyme A (CoA) is a useful biochemical research chemical, used in the preparation of high-yielding cell-free protein synthesis platforms. Coenzyme A hydrate has been used in the thiolase enzyme assay of recombinant acetoacetyl-CoA thiolase (rACAT) in Clonorchis sinensis. It may be used as a reference standard in Raman spectra measurements.

Technology Process of [[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate

There total 53 articles about [[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate 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:

glycine (56-40-6,18875-39-3,25718-94-9) + 2-methyl-3-butenoyl-CoA (6712-03-4) → N-3-methylbut-2-enoyl glycine (33008-07-0) + coenzyme A (85-61-0)

Guidance literature:

With bovine liver glycine N-acyltransferase; at 30 ℃; pH=8; Reagent/catalyst; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1124/dmd.111.041657

Reference yield:

glycine (56-40-6,18875-39-3,25718-94-9) + S-benzoyl coenzyme A (6756-74-7,25718-12-1) → Hippuric Acid (495-69-2,140480-84-8,21251-67-2,91787-63-2,66407-11-2) + coenzyme A (85-61-0)

Guidance literature:

With bovine liver glycine N-acyltransferase; at 30 ℃; pH=8; Reagent/catalyst; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1124/dmd.111.041657

Reference yield:

C22H38N7O17P3S → formaldehyd (50-00-0,30525-89-4,61233-19-0) + methanediol (463-57-0) + coenzyme A (85-61-0)

Guidance literature:

With phosphate buffer; In water; water-d2; Equilibrium constant;

DOI:10.1021/jo9616724

upstream raw materials:

pantothenic acid

GLUTATHIONE

coenzyme A disulfide

coenzyme A-glutathione mixed disulfide

Downstream raw materials:

acryloyl-CoA

acetylcoenzyme A

S-propionyl-coenzyme-A

fluoroacetyl coenzyme A

Refernces

• 1、 Michelson. "-". . . Retrieved 1964.
• 2、 Shimizu,Nagase,Okada,Hosokawa,Tagawa. "A total synthesis of coenzyme A via thiazoline intermediate.". . p. 1142 - 1144. Retrieved 1965.
• 3、 Sidorov,Zverkov,Shram,Lazurkina,Myasoedov. "Chemical and enzymatic synthesis of tritium labelled coenzymes". . p. 465 - 473. Retrieved 2003.
• 4、 Chang, Catherine C. Y.,Chang, Ta-Yuan,Chen, Lei,Chen, Si-Cong,Guan, Chengcheng,Kang, Yunlu,Luo, Tuoping,Nishi, Koji,Niu, Yange,Wu, Jing-Xiang. "Structural insights into the inhibition mechanism of human sterol O-acyltransferase 1 by a competitive inhibitor". . . Retrieved 2020/05/27.
• 5、 Schulz, Anne-Christine,Frielingsdorf, Stefan,Pommerening, Phillip,Lauterbach, Lars,Bistoni, Giovanni,Neese, Frank,Oestreich, Martin,Lenz, Oliver. "Formyltetrahydrofolate Decarbonylase Synthesizes the Active Site CO Ligand of O2-Tolerant [NiFe] Hydrogenase". . p. 1457 - 1464. Retrieved 2020/01/31.