Synonym
Lauroyl-coenzyme A; Dodecanoyl-coa; Lauroyl-coa; Coenzyme A, lauroyl-;
IUPAC/Chemical Name
S-(2-(3-((R)-4-(((S)-(((R)-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-3,3-dimethylbutanamido)propanamido)ethyl) dodecanethioate
InChi Key
YMCXGHLSVALICC-GMHMEAMDSA-N
InChi Code
InChI=1S/C33H58N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h20-22,26-28,32,43-44H,4-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/t22-,26-,27-,28+,32-/m1/s1
SMILES Code
OP(O[C@@H]1[C@@H](CO[P@@](O)(O[P@@](O)(OCC(C)([C@@H](O)C(NCCC(NCCSC(CCCCCCCCCCC)=O)=O)=O)C)=O)=O)O[C@@H](n(cn2)c3c2c(N)ncn3)[C@@H]1O)(O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
949.84
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Musayev F, Sachdeva S, Scarsdale JN, Reynolds KA, Wright HT. Crystal structure of a substrate complex of Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein synthase III (FabH) with lauroyl-coenzyme A. J Mol Biol. 2005 Mar 11;346(5):1313-21. Epub 2005 Jan 20. PubMed PMID: 15713483.
2: Poosch MS, Yamazaki RK. Determination of peroxisomal fatty acyl-CoA oxidase activity using a lauroyl-CoA-based fluorometric assay. Biochim Biophys Acta. 1986 Dec 10;884(3):585-93. PubMed PMID: 3778940.
3: Oba Y, Sato M, Ojika M, Inouye S. Enzymatic and genetic characterization of firefly luciferase and Drosophila CG6178 as a fatty acyl-CoA synthetase. Biosci Biotechnol Biochem. 2005 Apr;69(4):819-28. PubMed PMID: 15849423.
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5: Bieber LL, Wagner M. Effect of pH and acyl-CoA chain length on the conversion of heart mitochondrial CPT-I/CPTo to a high affinity, malonyl-CoA-inhibited state. Biochim Biophys Acta. 1996 Aug 13;1290(3):261-6. PubMed PMID: 8765129.
6: Bränström R, Aspinwall CA, Välimäki S, Ostensson CG, Tibell A, Eckhard M, Brandhorst H, Corkey BE, Berggren PO, Larsson O. Long-chain CoA esters activate human pancreatic beta-cell KATP channels: potential role in Type 2 diabetes. Diabetologia. 2004 Feb;47(2):277-83. Epub 2004 Jan 23. PubMed PMID: 14740158.
7: Cai Y, Appelkvist EL, DePierre JW. Hepatic oxidative stress and related defenses during treatment of mice with acetylsalicylic acid and other peroxisome proliferators. J Biochem Toxicol. 1995 Apr;10(2):87-94. PubMed PMID: 7562957.
8: Ramsey AJ, Chinkers M. Identification of potential physiological activators of protein phosphatase 5. Biochemistry. 2002 Apr 30;41(17):5625-32. PubMed PMID: 11969423.
9: Gallagher EP, Di Giulio RT. Effects of 2,4-dichlorophenoxyacetic acid and picloram on biotransformation, peroxisomal and serum enzyme activities in channel catfish (Ictalurus punctatus). Toxicol Lett. 1991 Jun;57(1):65-72. PubMed PMID: 2048162.
