Maltoside

A maltoside is a glycoside with maltose as the glycone (sugar) functional group. Among the most common are alkyl maltosides, which contain hydrophobic alkyl chains as the aglycone. Given their amphiphilic properties, these comprise a class of detergents, where variation in the alkyl chain confers a range of detergent properties including CMC and solubility. Maltosides are most often used for the solubilization and purification of membrane proteins.

Chemical structure of n-decyl-β-D-maltopyranoside (DM)

History

In 1980 Ferguson-Miller et al. at Michigan State developed n-dodecyl-β-D-maltopyranoside (DDM) as part of a successful effort to purify an active, stable, monodisperse form of cytochrome c oxidase.^[1] Maltosides have been used extensively to stabilize membrane proteins for biophysical and structural studies.

Table of detergent properties

Maltoside	abbr.	CMC (mM)	MW (g/mol)	Micelle (kDa)
n-Decyl-β-D-maltopyranoside	DM	1.8 [2] (H2O)	482.6	~33 (69 molecules)
n-Dodecyl-β-D-maltopyranoside	DDM	0.17 [3]	510.6	~72 (~78-149 molecules)[4]
6-Cyclohexyl-1-hexyl-β-D-maltopyranoside	Cymal-6	0.56	508.5	46.3