# Maltoside

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{{Short description|Class of chemical compounds}}
thumb|right|Chemical structure of ''n''-decyl-β-D-maltopyranoside (DM)
A '''maltoside''' is a [glycoside](/source/glycoside) with [maltose](/source/maltose) as the glycone (sugar) [functional group](/source/functional_group). Among the most common are '''alkyl maltosides''', which contain hydrophobic [alkyl chain](/source/alkyl_chain)s as the [aglycone](/source/aglycone). Given their [amphiphilic](/source/amphiphilic) properties, these comprise a class of [detergent](/source/detergent)s, where variation in the alkyl chain confers a range of detergent properties including [CMC](/source/Critical_micelle_concentration) and solubility. Maltosides are most often used for the solubilization and purification of [membrane protein](/source/membrane_protein)s.

== History ==
In 1980 Ferguson-Miller ''et al.'' at Michigan State developed ''n''-dodecyl-β-<small>D</small>-maltopyranoside (DDM) as part of a successful effort to purify an active, stable, monodisperse form of [cytochrome c oxidase](/source/cytochrome_c_oxidase).<ref>{{cite journal|last1=Rosevear|first1=P|last2=VanAken |first2=T |last3=Baxter |first3=J |last4=Ferguson-Miller |first4=S |title=Alkyl glycoside detergents: a simpler synthesis and their effects on kinetic and physical properties of cytochrome c oxidase.|journal=Biochemistry|date=Aug 19, 1980|volume=19|issue=17|pages=4108–15|pmid=6250583|doi=10.1021/bi00558a032}}</ref>  Maltosides have been used extensively to stabilize membrane proteins for biophysical and structural studies.

== Table of detergent properties ==
{| class="wikitable"
|-
! Maltoside !! abbr. !! [CMC](/source/Critical_micelle_concentration) (mM) !! MW (g/mol) !! Micelle (kDa)
|-
| ''n''-Decyl-β-<small>D</small>-maltopyranoside || DM || 1.8 <ref>{{cite journal |last1=Alpes |first1=H. |last2=Apell |first2=H.-J. |last3=Knoll |first3=G. |last4=Plattner |first4=H. |last5=Riek |first5=R. |title=Reconstitution of Na+/K+-ATPase into phosphatidylcholine vesicles by dialysis of nonionic alkyl maltoside detergents |journal=Biochimica et Biophysica Acta (BBA) - Biomembranes |date=December 1988 |volume=946 |issue=2 |pages=379–388 |doi=10.1016/0005-2736(88)90413-0|pmid=2850005 }}</ref> (H<sub>2</sub>O) || 482.6 || ~33 (69 molecules)
|-
| ''n''-Dodecyl-β-<small>D</small>-maltopyranoside || DDM || 0.17 <ref>{{cite book |last1=Vanaken |first1=T. |last2=Foxall-Vanaken |first2=S. |last3=Castleman |first3=S. |last4=Ferguson-Miller |first4=S.  | chapter = Alkyl glycoside detergents: Synthesis and applications to the study of membrane proteins | title = Biomembranes Part M | year = 1986 | volume = 125 | pages = 27–35 | doi = 10.1016/S0076-6879(86)25005-3 | pmid = 3012259 | series = Methods in Enzymology | isbn = 9780121820251}}</ref> || 510.6 || ~72 (~78-149 molecules)<ref>{{cite journal |last1=Strop |first1=Pavel |last2=Brunger |first2=Axel T. |title=Refractive index-based determination of detergent concentration and its application to the study of membrane proteins |journal=Protein Science |date=August 2005 |volume=14 |issue=8 |pages=2207–2211 |doi=10.1110/ps.051543805|pmid=16046633 |pmc=2279333 }}</ref>
|-
| 6-Cyclohexyl-1-hexyl-β-<small>D</small>-maltopyranoside || Cymal-6 || 0.56 || 508.5 || 46.3
|}

==References==
{{Reflist}}

Category:Disaccharides
Category:Reagents for biochemistry
Category:Non-ionic surfactants

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Adapted from the Wikipedia article [Maltoside](https://en.wikipedia.org/wiki/Maltoside) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Maltoside?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.