Coenzyme A
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| Category | Raw Materials of Healthcare Products |
| Catalog number | BBF-05821 |
| CAS | 85-61-0 |
| Molecular Weight | 767.53 |
| Molecular Formula | C21H36N7O16P3S |
| Purity | >85% |
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Description
Coenzyme A is an essential metabolic cofactor synthesized from cysteine, pantothenate, and ATP. Coenzyme A plays important roles in many metabolic pathways, including the tricarboxylic acid cycle, and the synthesis and oxidation of fatty acids. About 4% of cellular enzymes utilize CoA as a substrate.
Specification
| Synonyms | CoASH; Coenzyme A (free acid); Depot-Zeel; Coenzyme ASH; 3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl] dihydrogen diphosphate} |
| Shelf Life | 1 Year |
| Storage | Store at -20°C |
| IUPAC Name | [[(2R,3S,4R,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 |
| 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 |
| InChI | InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1 |
| InChI Key | RGJOEKWQDUBAIZ-IBOSZNHHSA-N |
Properties
| Appearance | White or Yellowish Powder |
| Boiling Point | 146 - 147 |
| Melting Point | -5°C |
| Density | 1.96±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Water |
Reference Reading
1. Acyl Glucuronide and Coenzyme A Thioester Metabolites of Carboxylic Acid-Containing Drug Molecules: Layering Chemistry with Reactive Metabolism and Toxicology
Kaushik Mitra Chem Res Toxicol. 2022 Oct 17;35(10):1777-1788. doi: 10.1021/acs.chemrestox.2c00188. Epub 2022 Oct 6.
Glucuronidation and CoA (coenzyme A) conjugation are common pathways for the elimination of carboxylic acid-containing drug molecules. In some instances, these biotransformations have been associated with toxicity (such as idiosyncratic hepatic injury, renal impairment, hemolytic anemia, gastrointestinal inflammation, and bladder cancer) attributed to, in part, the propensity of acyl glucuronides and acyl CoA thioesters to covalently modify biological macromolecules such as proteins and DNA. It is to be noted that, while acyl glucuronidation and CoA conjugation are indeed implicated in adverse effects, there are many safe drugs in the market that are cleared by these reactive pathways. It is therefore important that new molecular entities with carboxylic acid groups are evaluated for toxicity in a manner that is not unreasonably risk-averse. In the absence of truly predictable methods, therefore, the general approach is to apply a set of end points to generate a weight-of-evidence evaluation. In practice, the focus is to identify structural liabilities and provide structure-activity recommendations early in the program, at a stage where an attempt to improve reactive metabolism does not deoptimize other critical drug-quality criteria. This review will present a high-level overview of the chemistry of glucuronidation and CoA conjugation and provide a discussion of the possible mechanisms of adverse effects that have been associated with these pathways, as well as how such potential hazards are addressed while delivering a new chemical entity for clinical evaluation.
2. Coenzyme A precursors flow from mother to zygote and from microbiome to host
Yi Yu, Marianne van der Zwaag, Jouke Jan Wedman, Hjalmar Permentier, Niels Plomp, Xiu Jia, Bart Kanon, Ellie Eggens-Meijer, Girbe Buist, Hermie Harmsen, Jan Kok, Joana Falcao Salles, Bregje Wertheim, Susan J Hayflick, Erick Strauss, Nicola A Grzeschik, Hein Schepers, Ody C M Sibon Mol Cell. 2022 Jul 21;82(14):2650-2665.e12. doi: 10.1016/j.molcel.2022.05.006. Epub 2022 Jun 3.
Coenzyme A (CoA) is essential for metabolism and protein acetylation. Current knowledge holds that each cell obtains CoA exclusively through biosynthesis via the canonical five-step pathway, starting with pantothenate uptake. However, recent studies have suggested the presence of additional CoA-generating mechanisms, indicating a more complex system for CoA homeostasis. Here, we uncovered pathways for CoA generation through inter-organismal flows of CoA precursors. Using traceable compounds and fruit flies with a genetic block in CoA biosynthesis, we demonstrate that progeny survive embryonal and early larval development by obtaining CoA precursors from maternal sources. Later in life, the microbiome can provide the essential CoA building blocks to the host, enabling continuation of normal development. A flow of stable, long-lasting CoA precursors between living organisms is revealed. This indicates the presence of complex strategies to maintain CoA homeostasis.
3. Coenzyme A thioester-mediated carbon chain elongation as a paintbrush to draw colorful chemical compounds
Shenghu Zhou, Tingting Hao, Shumin Xu, Yu Deng Biotechnol Adv. 2020 Nov 1;43:107575. doi: 10.1016/j.biotechadv.2020.107575. Epub 2020 Jun 5.
The biosynthesis of various useful chemicals from simple substrates using industrial microorganisms is becoming increasingly crucial to address the challenge of dwindling non-renewable resources. As the most common intermediate substrates in organisms, Coenzyme A (CoA) thioesters play a central role in the carbon chain elongation process of their products. As a result, numerous of chemicals can be synthesized by the iterative addition of various CoA thioester extender units at a given CoA thioester primer backbone. However, these elongation reactions and the product yields are still restricted due to the low enzymatic performance and supply of CoA thioesters. This review highlights the current protein and metabolic engineering strategies used to enhance the diversity and product yield by coupling different primers, extender units, enzymes, and termination pathways, in an attempt to provide a road map for producing a more diverse range of industrial chemicals.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
