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Key Documents

C2643

Sigma-Aldrich

Coenzyme A, oxidized lithium salt

≥85%

Synonym(s):

CoA-S-S-CoA

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5 MG
$168.30
10 MG
$315.30

About This Item

Empirical Formula (Hill Notation):
C42H70N14O32P6S2 · xLi+
CAS Number:
31664-36-5
Molecular Weight:
1533.05 (free acid basis)
UNSPSC Code:
41106305
PubChem Substance ID:
24892510
NACRES:
NA.51

$168.30

List Price$187.00Save 10%
Web-Only Promotion

Available to ship onMay 01, 2025Details

assay

≥85%

form

solid

storage temp.

−20°C

SMILES string

[P](=O)(O[P](=O)(OCC([C@@H](O)C(=O)NCCC(=O)NCCSSCCNC(=O)CCNC(=O)[C@H](O)C(CO[P](=O)(O[P](=O)(OC[C@H]4O[C@H]([C@@H]([C@@H]4O[P](=O)(O)O)O)[n]5c6ncnc(c6nc5)N)O)O)(C)C)(C)C)O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O[P](=O)(O)O)O)[n]2c3ncnc(c3nc2)N)O

InChI

1S/C42H70N14O32P6S2/c1-41(2,15-81-93(75,76)87-91(71,72)79-13-21-29(85-89(65,66)67)27(59)39(83-21)55-19-53-25-33(43)49-17-51-35(25)55)31(61)37(63)47-7-5-23(57)45-9-11-95-96-12-10-46-24(58)6-8-48-38(64)32(62)42(3,4)16-82-94(77,78)88-92(73,74)80-14-22-30(86-90(68,69)70)28(60)40(84-22)56-20-54-26-34(44)50-18-52-36(26)56/h17-22,27-32,39-40,59-62H,5-16H2,1-4H3,(H,45,57)(H,46,58)(H,47,63)(H,48,64)(H,71,72)(H,73,74)(H,75,76)(H,77,78)(H2,43,49,51)(H2,44,50,52)(H2,65,66,67)(H2,68,69,70)/t21-,22-,27-,28-,29-,30-,31+,32+,39-,40-/m1/s1

InChI key

YAISMNQCMHVVLO-ODFVJXNFSA-N

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General description

Coenzyme A (CoA) is a ubiquitous cofactor present in all living organisms.[1] It is synthesized by the enzymatic conjugation of cysteine, pantothenate (Vitamin B5), and adenosine triphosphate (ATP).[2]

Application

Coenzyme A oxidized lithium salt has been used in the preparation of the coenzyme A persulfide (CoASSH) standard to quantify the CoASSH in Staphylococcus aureus strains by tandem mass spectrometry.[3]

Biochem/physiol Actions

Coenzyme A (CoA) plays a role as an acyl-group carrier and carbonyl activator in several biochemical reactions like the tricarboxylic acid cycle and fatty acid metabolism. It acts as a co-factor for several enzymes and is involved in several reactions in intermediary metabolism.[1] CoA contains a thiol group that enables it to take part in several biochemical reactions.[2] Oxidized CoA may be used to study reduction systems (CoA disulfide reductase (CoADR) systems) that regenerate reduced CoA in vivo. Furthermore, oxidized CoA may be used to study the unique functions of this molecule in vivo.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H315,H318

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000368676
0000368676
SLCM7634
SLBF5065V
SLBF5065

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Charles S Hummel et al.
FEMS microbiology letters, 252(2), 229-234 (2005-10-11)
Physiologically significant levels of intracellular coenzyme A were identified in Pyrococcus furiosus, Thermococcus litoralis, and Sulfolobus solfataricus, suggesting a role for CoA as an important low molecular mass thiol in the thermophilic Archaea. In P. furiosus, cells grown in the
Julie A Boylan et al.
Molecular microbiology, 59(2), 475-486 (2006-01-05)
The cellular responses of Borrelia burgdorferiTo reactive oxygen species (ROS) encountered during the different stages of its infective cycle are poorly understood. Few enzymes responsible for protecting proteins, DNA/RNA and lipids from damage by ROS have been identified and characterized.
V M Avakumov et al.
Eksperimental'naia i klinicheskaia farmakologiia, 56(1), 42-44 (1993-01-01)
Coenzyme A disulfide (CoA disulfide) was pharmacologically studied. It has been found to normalize lipid and carbohydrate metabolism when given in a dose of 2 mg/kg, i.m., in diverse liver dysfunctions. It possesses an antihypoxic action under hemic and histotoxic
S B delCardayre et al.
The Journal of biological chemistry, 273(10), 5752-5757 (1998-04-16)
The cdr gene encoding coenzyme A disulfide reductase (CoADR) from Staphylococcus aureus 8325-4 was cloned, sequenced, and overexpressed. The gene encodes a 438-amino acid polypeptide that has a calculated molecular weight of 49,200 and sequence similarity to the pyridine nucleotide-disulfide
J Luba et al.
Biochemistry, 38(9), 2725-2737 (1999-03-03)
An unusual flavoprotein disulfide reductase, which catalyzes the NADPH-dependent reduction of CoASSCoA, has recently been purified from the human pathogen Staphylococcus aureus [delCardayré, S. B., Stock, K. P., Newton, G. L., Fahey, R. C., and Davies, J. E. (1998) J.
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