Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and CHAPS detergent: Difference between pages

| Watchedfields = changed

| verifiedrevid = 470456710

| ImageFile = CHAPS.png

| ImageName = Structural formula of CHAPS detergent

| IUPACName = 3-<nowiki/>{Dimethyl[3-(3α,7α,12α-trihydroxy-5β-cholan-24-amido)propyl]azaniumyl}propane-1-sulfonate

| SystematicName = 3-[Dimethyl(3-<nowiki/>{(4''R'')-4-[(1'''R'',3a''S'',3b''R'',4''R'',5a''S'',7''R'',9a''S'',9b''S'',11''S'',11a''R'')-4,7,11-trihydroxy-9a,11a-dimethylhexadecahydro-1''H''-cyclopenta[''a'']phenanthren-1-yl]pentanamido}propyl)azaniumyl]propane-1-sulfonate

| OtherNames = 3-[(3-Cholamidopropyl)dimethylammonio]-1-propanesulfonate

|Section1={{Chembox Identifiers

| Abbreviations = CHAPS

| InChI = 1/C32H58N2O7S/c1-21(8-11-29(38)33-14-6-15-34(4,5)16-7-17-42(39,40)41)24-9-10-25-30-26(20-28(37)32(24,25)3)31(2)13-12-23(35)18-22(31)19-27(30)36/h21-28,30,35-37H,6-20H2,1-5H3,(H-,33,38,39,40,41)/t21-,22+,23-,24-,25+,26+,27-,28+,30+,31+,32-/m1/s1

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = QBP25342AG

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| PubChem1 = 24883538

| PubChem1_Comment = (),(5''R'',7''S'',<br />

| PubChem2 = 10371606

| PubChem2_Comment = (),(1''S'',5''R'',11''S'',<br />

| PubChem3 = 25244640

| PubChem3_Comment = (4''R''),(2''S'',5''R'',7''S'',<br />

| PubChem4 = 18397788

| PubChem4_Comment = (4''R''),(2''S'',5''R'',<br />

| PubChem5 = 9895216

| PubChem5_Comment = (4''S''),<br />

| ChemSpiderID = 96843

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = 3-((3-Cholamidopropyl)dimethylammonium)-1-propanesulfonate

| SMILES = CC(CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C32H58N2O7S/c1-21(8-11-29(38)33-14-6-15-34(4,5)16-7-17-42(39,40)41)24-9-10-25-30-26(20-28(37)32(24,25)3)31(2)13-12-23(35)18-22(31)19-27(30)36/h21-28,30,35-37H,6-20H2,1-5H3,(H-,33,38,39,40,41)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UMCMPZBLKLEWAF-UHFFFAOYSA-N}}

|Section2={{Chembox Properties

| C=32 | H=58 | N=2 | O=7 | S=1

| LogP = &minus;4.32 (predicted)

| CMC =8-10 mM

| HLB =

'''CHAPS''' is a [[zwitterion]]ic [[surfactant]] used in the laboratory to [[solubility|solubilize]] biological macromolecules such as [[protein]]s. It may be synthesized from [[cholic acid]]<ref>{{cite journal|last1=Hjelmeland|first1=LM|title=A nondenaturing zwitterionic detergent for membrane biochemistry: design and synthesis.|journal=Proceedings of the National Academy of Sciences of the United States of America|date=November 1980|volume=77|issue=11|pages=6368–70|pmid=6935651|doi=10.1073/pnas.77.11.6368|pmc=350285|bibcode=1980PNAS...77.6368H|doi-access=free}}</ref> and is zwitterionic due to its [[quaternary ammonium]] and [[sulfonate]] groups; it is structurally similar to certain [[bile acid]]s, such as [[taurodeoxycholic acid]] and [[taurochenodeoxycholic acid]]. It is used as a non-[[Denaturation (biochemistry)|denaturing]] detergent in the process of [[protein purification]] and is especially useful in purifying [[membrane protein]]s, which are often sparingly soluble or insoluble in [[aqueous]] solution due to their native [[hydrophobic|hydrophobicity]].<ref name="CladeraRicaud1997">{{cite journal|last1=Cladera|first1=Josep|last2=Ricaud|first2=Jean-Louis|last3=Verde|first3=Joaquim Villa|last4=DuNach|first4=Mireia|title=Liposome Solubilization and Membrane Protein Reconstitution Using Chaps and Chapso|journal=European Journal of Biochemistry|volume=243|issue=3|year=1997|pages=798–804|doi=10.1111/j.1432-1033.1997.00798.x|pmid=9057848|doi-access=free}}</ref>

CHAPS is an abbreviation for 3-[(3-'''ch'''olamidopropyl)dimethyl'''a'''mmonio]-1-'''p'''ropane'''s'''ulfonate. 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 monitoring ongoing [[chemical reaction]]s or [[protein-protein interaction|protein-protein binding]] with [[UV/Vis spectroscopy]].

==See also==

* [[Taurodeoxycholic acid]]

* [[Taurochenodeoxycholic acid]]

==References==

{{Reflist}}

[[Category:Steroids]]

[[Category:Biochemistry methods]]

[[Category:Zwitterionic surfactants]]