3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate

Catalog Number	ACM82473243-1
CAS	82473-24-3
Structure
Synonyms	CHAPSO
IUPAC Name	3-[Dimethyl-[3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propyl]azaniumyl]-2-hydroxypropane-1-sulfonate
Molecular Weight	630.9
Molecular Formula	C32H58N2O8S
Canonical SMILES	CC(CCC(=O)NCCC[N+](C)(C)CC(CS(=O)(=O)[O-])O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
InChI	InChI=1S/C32H58N2O8S/c1-20(7-10-29(39)33-13-6-14-34(4,5)18-23(36)19-43(40,41)42)24-8-9-25-30-26(17-28(38)32(24,25)3)31(2)12-11-22(35)15-21(31)16-27(30)37/h20-28,30,35-38H,6-19H2,1-5H3,(H-,33,39,40,41,42)/t20-,21+,22-,23?,24-,25+,26+,27-,28+,30+,31+,32-/m1/s1
InChI Key	GUQQBLRVXOUDTN-XOHPMCGNSA-N
Melting Point	184-186 °C
Purity	98%+
Complexity	1070
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	11
Exact Mass	630.39138799
Heavy Atom Count	43
Hydrogen Bond Acceptor Count	8
Hydrogen Bond Donor Count	5
Isomeric SMILES	C[C@H](CCC(=O)NCCC[N+](C)(C)CC(CS(=O)(=O)[O-])O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Monoisotopic Mass	630.39138799
Physical State	Solid
Rotatable Bond Count	11
Topological Polar Surface Area	176 Ų

Knowledge & Learning Case Study Q&A

3-[(3-Cholamidopropyl)dimethylammonio]-2-Hydroxy-1-Propanesulfonate Used in Coq2p Activity Assay

Burón MI, et al. Analytical Biochemistry, 2006, 353(1), 15-21.

The use of 3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate and sodium cholate instead of Triton X-100 offers a more sensitive and efficient Coq2p assay. 3-[(cholamidopropyl)dimethylammonio]-1-propanesulfonate (CHAPS) and sodium cholate significantly enhance enzyme activity more than Triton X-100. This method is applicable to various biological samples and aids in the investigation of ubiquinone biosynthesis and associated deficiencies.
Materials
Buffers: 50 mM phosphate buffer (pH 7.5), 10 mM MgCl₂, 5 mM EGTA.
Inhibitors: 1 mM PMSF, 20 µg/mL each of chymostatin, leupeptin, antipain, and pepstatin A.
Substrate: 5 µM solanesyl pyrophosphate.
Detergents: Tested at up to 1% concentration (Triton X-100, CHAPS, sodium cholate, others).
Radiolabel: 105 DPM of [U-14C]pHB.
Method
Sample Preparation: Combine crude homogenates or isolated mitochondria (0.1-1 mg protein) with assay buffer and protease inhibitors.
Reaction Setup: Add solanesyl pyrophosphate and detergent to the sample. Incubate for 30 minutes at 37°C with gentle stirring.
Reaction Termination: Cool to 4°C to stop the reaction.
Lipid Extraction: Add SDS and a mixture of ethanol and isopropanol, followed by hexane for phase separation. Recover prenylated [U-14C]pHB from the organic phase.
Radioactivity Measurement: Mix with scintillation cocktail and measure radioactivity using a scintillation counter.
Controls
Boiled Protein: Test protein stability by boiling for 3 minutes.
No Solanesyl Pyrophosphate: Exclude solanesyl pyrophosphate to ensure reaction specificity.

3-[(3-Cholamidopropyl)dimethylammonio]-2-Hydroxy-1-Propanesulfonate Used in Lubrication

Xu X, et al. Tribology International, 2020, 151, 106441.

3-[(3-Cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate (CHAPS) is a superior additive for improving lubrication, especially on steel/ceramic interfaces, due to its positive impact on electroosmosis and penetration. By analyzing the effects of cationic (cetyltrimethylammonium bromide, CTAB) and zwitterionic (CHAPS) additives on the electroosmotic properties of lubricants, this study assesses their tribological performance on steel/steel and steel/ceramic interfaces. The study provides insights into optimizing lubricant formulations, enhancing their effectiveness in reducing friction and wear through targeted electroosmotic strategies.
Lubricant Preparation
Pure water served as the base fluid. CHAPS and CTAB were dispersed ultrasonically into the base fluid to create AS lubricants.
Further, 0.1 wt% SiO2 nanoparticles of 20-30 nm in diameter were added to pure water and ultrasonically de-agglomerated for 30 min to prepare another base fluid. Then, CHAPS and CTAB were, respectively, ultrasonically dispersed into this base fluid. These nanoparticle suspensions were named NPs lubricant. The concentrations of CHAPS and CTAB in the AS and NPs lubricants were 0.0125, 0.05, 0.1, and 0.2 mmol/L.
Tribological Performance
Friction and Wear Reduction:
CHAPS: Significantly reduces the coefficient of friction (COF) and wear scar diameter (WSD) at both interfaces, with greater effects observed on steel/ceramic interfaces.
CTAB: Increases COF and WSD, particularly on steel/ceramic interfaces.
Elemental Analysis:
CHAPS: Increases Si content on worn surfaces in NPs lubricants, more so on steel/ceramic interfaces.
CTAB: Decreases Si content, reducing its effectiveness.
Mechanism
CHAPS enhances capillary penetrability, improving anti-friction and anti-wear properties. It effectively promotes electroosmosis, aiding lubricant penetration.
CTAB suppresses capillary penetration, leading to poorer tribological performance.

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