dephospho-CoA

Base Information

• Chemical Name: dephospho-CoA
• CAS No.: 3633-59-8
• Molecular Formula: C21H35 N7 O13 P2 S
• Molecular Weight: 687.562
• Nikkaji Number: J1.407.433C
• Wikidata: Q27089453
• Metabolomics Workbench ID: 49924
• Mol file: 3633-59-8.mol

Synonyms:2'-(5''-triphosphoribosyl)-3'-dephospho-CoA;3'-desphospho-coenzyme A;dephospho CoA;dephospho-CoA;dephosphocoenzyme A;desphospho-CoA;dpCoA

Chemical Property of dephospho-CoA

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 1.16±0.50(Predicted)
• Flash Point: °C
• PSA: 358.45000
• Density: 1.85g/cm³
• LogP: -0.41930
• Storage Temp.: −20°C
• XLogP3: -4.7
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 16
• Exact Mass: 687.14887937
• Heavy Atom Count: 44
• Complexity: 1100

Purity/Quality:

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

3′-Dephosphocoenzyme A ≥90% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)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)O)[C@H](C(=O)NCCC(=O)NCCS)O
• Description: 3''-Dephosphocoenzyme A is an intermediate in the biosynthesis of coenzyme A (CoA; Item Nos. 16147 | 21499 | 21722) from pantothenic acid (vitamin B5; ). It is phosphorylated by CoA synthase in humans to form CoA. 3''-Dephosphocoenzyme A can be used as a transcription initiator in the synthesis of CoA-RNA by in vitro transcription.
• Uses: Dephosphocoenzyme A is the direct precursor of coenzyme A. It is used for the synthesis of coenzyme A by bifunctional CoA Synthase (CoASy, 4′-phosphopantetheine adenylyltransferase/dephospho-CoA kinase) which performs the transfer of the γ-phosphate of ATP to dephosphocoenzyme A.

Technology Process of dephospho-CoA

There total 8 articles about dephospho-CoA 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:

D‐pantetheine 4'‐phosphate (2226-71-3,105974-69-4,13147-30-3,137044-41-8) + ATP (56-65-5,896506-78-8) → 3′-dephospho-coenzyme A (3633-59-8)

Guidance literature:

With pyruvate kinase; human phosphopantethiene adenylyltransferase; magnesium chloride; In various solvent(s); at 20 ℃; pH=6.0;

DOI:10.1039/b512735a

Reference yield:

coenzyme A (85-61-0) → 3′-dephospho-coenzyme A (3633-59-8)

Guidance literature:

With raygras phosphatase;

DOI:10.1002/hlca.19560390638

Reference yield:

(R)-Pantolacton (599-04-2) → 3′-dephospho-coenzyme A (3633-59-8)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / ethanol / Inert atmosphere; Reflux

2: tris-(2-carboxyethyl)-phosphine hydrochloride; potassium chloride; magnesium chloride / aq. buffer / pH 7.5 / Inert atmosphere

3: potassium chloride; magnesium chloride; ATP; pantetheine kinase / aq. buffer / 2 h / 20 °C / pH 7.5 / Inert atmosphere; Enzymatic reaction

4: potassium chloride; magnesium chloride; phosphopantetheine adenyltransferase / aq. buffer / 20 °C / pH 7.5 / Inert atmosphere; Enzymatic reaction

With phosphopantetheine adenyltransferase; pantetheine kinase; potassium chloride; tris-(2-carboxyethyl)-phosphine hydrochloride; triethylamine; ATP; magnesium chloride; In ethanol;

DOI:10.1021/acs.oprd.6b00059

upstream raw materials:

coenzyme A

D‐pantetheine 4'‐phosphate

ATP

(R)-Pantolacton

Downstream raw materials:

acetyl-coenzyme A

coenzyme A

Refernces

• 1、 Wubben, Thomas J.,Mesecar, Andrew D.. "Kinetic, Thermodynamic, and Structural Insight into the Mechanism of Phosphopantetheine Adenylyltransferase from Mycobacterium tuberculosis". . p. 202 - 219. Retrieved 2010.
• 2、 Worthington, Andrew S.,Burkart, Michael D.. "One-pot chemo-enzymatic synthesis of reporter-modified proteins". . p. 44 - 46. Retrieved 2007/10/03.