CHAPS detergent

CHAPS detergent
Names
Preferred IUPAC name
3-[(3-Cholamidopropyl)dimethylammonio]-1-
propanesulfonate
Systematic IUPAC name
3-{Dimethyl[3-(4-{5,9,16-trihydroxy-2,15-

dimethyltetracyclo[8.7.0.02,7.011,15]
heptadecan-14-yl}pentanamido)propyl]

azaniumyl}propane-1-sulfonate
Other names
3-{Dimethyl[3-(4-{5,9,16-trihydroxy-2,15-

dimethyltetracyclo[8.7.0.02,7.011,15]
heptadecan-14-yl}pentanamido)propyl]aminio}

propane-1-sulfonate
Identifiers
75621-03-3 YesY
3D model (Jmol) Interactive image
Interactive image
Abbreviations CHAPS
ChEMBL ChEMBL450950 YesY
ChemSpider 96843 YesY
ECHA InfoCard 100.129.679
KEGG C11321 YesY
MeSH 3-((3-Cholamidopropyl)dimethylammonium)-1-propanesulfonate
PubChem 107670
24883538 (),(5R,7S,

16S)
10371606 (),(1S,5R,11S,
16S)
25244640 (4R),(2S,5R,7S,
15R,16S)
18397788 (4R),(2S,5R,
14R,15R,16S)
9895216 (4S),
(2S,5R,14R,15S,16S)

Properties
C32H58N2O7S
Molar mass 614.88 g·mol−1
Surface tension:
8-10 mM
log P −4.32 (predicted)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

CHAPS is a zwitterionic surfactant used in the laboratory to solubilize biological macromolecules such as proteins. It may be synthesized from cholic acid[1] and is zwitterionic due to its quaternary ammonium and sulfonate groups; it is structurally similar to certain bile acids, such as taurodeoxycholic acid and taurochenodeoxycholic acid. It is used as a non-denaturing solvent in the process of protein purification and is especially useful in purifying membrane proteins, which are often sparingly soluble or insoluble in aqueous solution due to their native hydrophobicity.[2]

CHAPS is an abbreviation for 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate. A related detergent, called CHAPSO, has the same basic chemical structure with an additional hydroxyl functional group; its full chemical name is 3-[(3-cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulfonate. Both detergents have low light absorbance in the ultraviolet region of the electromagnetic spectrum, which is useful for laboratory workers monitoring ongoing chemical reactions or protein-protein binding with UV/Vis spectroscopy.

See also

References

  1. ↑ Hjelmeland, LM (November 1980). "A nondenaturing zwitterionic detergent for membrane biochemistry: design and synthesis.". Proceedings of the National Academy of Sciences of the United States of America. 77 (11): 6368–70. doi:10.1073/pnas.77.11.6368. PMC 350285Freely accessible. PMID 6935651.
  2. ↑ Cladera, Josep; Ricaud, Jean-Louis; Verde, Joaquim Villa; DuNach, Mireia (1997). "Liposome Solubilization and Membrane Protein Reconstitution Using Chaps and Chapso". European Journal of Biochemistry. 243 (3): 798–804. doi:10.1111/j.1432-1033.1997.00798.x. ISSN 0014-2956.
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