CHAPSO
Product Information
Molecular Formula
C32H58N2O8S
Molecular Weight
630.88
Description
CHAPSO (3-[(3-Cholamidopropyl)-dimethylammonio]-2-hydroxy-1-propanesulfonate) is a hydroxylated derivative of CHAPS that combines enhanced hydrophilicity with the same steroidal backbone to improve protein stabilization and micellar uniformity. The additional hydroxyl group increases solvation and reduces aggregation, making CHAPSO ideal for solubilizing membrane proteins in conditions where traditional detergents are too harsh. It forms small, monodisperse micelles that preserve functional protein–lipid interactions. CHAPSO is widely employed in cryo-electron microscopy, structural proteomics, and reconstitution of fragile membrane assemblies, offering a refined balance between solubilization efficiency and preservation of biological activity in delicate lipid–protein complexes.
Synonyms
3-((3-cholamidopropyl)dimethylammonio)-2-hydroxy-1-propanesulfonate
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
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(lit.)
Flash Point
320 °F
Purity
Purity >98%
Appearance
White Crystalline Powder
Shelf Life
1 Year
Storage
Store at -20°C
Computed Properties
XLogP3
1.9
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
11
Exact Mass
630.39138799 g/mol
Monoisotopic Mass
630.39138799 g/mol
Topological Polar Surface Area
176Ų
Heavy Atom Count
43
Formal Charge
0
Complexity
1070
Isotope Atom Count
0
Defined Atom Stereocenter Count
11
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114137222-A | Kit for detecting tissue metal protease inhibitor-1 in body fluid sample | 2021-11-22 |
| CN-113564051-A | Cell mass digestion dissociation liquid and cell counting method | 2021-07-07 |
| CN-113278048-A | Purification method of membrane protein | 2021-05-26 |
| CN-113061591-A | Novel firefly luciferase mutant, preparation method and application thereof | 2021-03-31 |
| CN-113061591-B | Novel firefly luciferase mutant, preparation method and application thereof | 2021-03-31 |
| US-2022077449-A1 | Electrochemical cells, components thereof, and methods of their manufacture | 2020-09-08 |
| WO-2022049294-A1 | Method for detecting contaminating lipase activity | 2020-09-07 |
| WO-2022049211-A1 | Methods for the preparation of bioconjugates | 2020-09-02 |
| WO-2022042542-A1 | A fusion protein as a subunit vaccine immunogen against sars-cov-2 and preparation method thereof | 2020-08-27 |
| WO-2022046900-A1 | Methods and reagents for rapid detection of pathogens in biological samples | 2020-08-25 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22257923 | 2012-01-09 | High-throughput crystallization of membrane proteins using the lipidic bicelle method | Journal of visualized experiments : JoVE |
| 20235510 | 2010-04-08 | Interactions of hemin with model erythrocyte membranes | The journal of physical chemistry. B |
| 18480063 | 2008-07-11 | Phosphoinositides suppress gamma-secretase in both the detergent-soluble and -insoluble states | The Journal of biological chemistry |
| 17663636 | 2007-01-01 | Biochemical properties of endogenous presenilin 1 and presenilin 2 in cultured human B-lymphocytes | Clinical chemistry and laboratory medicine |
| 15912955 | 2005-03-01 | 3-O-alkyl-D-glucose derivatives induce fruit bodies of Pleurotus ostreatus | Mycological research |
| 15456764 | 2004-12-03 | Nicastrin, presenilin, APH-1, and PEN-2 form active gamma-secretase complexes in mitochondria | The Journal of biological chemistry |
| 15592142 | 2004-10-01 | Alzheimer amyloid precursor aspartyl proteinase activity in CHAPSO homogenates of Spodoptera frugiperda cells | Alzheimer disease and associated disorders |
| 15341515 | 2004-09-01 | Conserved residues within the putative active site of gamma-secretase differentially influence enzyme activity and inhibitor binding | Journal of neurochemistry |
| 15222759 | 2004-07-06 | Effect of membrane perturbants on the activity and phase distribution of inositol phosphorylceramide synthase; development of a novel assay | Biochemistry |
| 12857757 | 2003-09-26 | Assembly of the gamma-secretase complex involves early formation of an intermediate subcomplex of Aph-1 and nicastrin | The Journal of biological chemistry |
