Maltoside

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

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.

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

References

1. Rosevear, P; VanAken, T; Baxter, J; Ferguson-Miller, S (Aug 19, 1980). "Alkyl glycoside detergents: a simpler synthesis and their effects on kinetic and physical properties of cytochrome c oxidase". Biochemistry. 19 (17): 4108–15. doi:10.1021/bi00558a032. PMID   6250583.
2. Alpes, H.; Apell, H.-J.; Knoll, G.; Plattner, H.; Riek, R. (December 1988). "Reconstitution of Na+/K+-ATPase into phosphatidylcholine vesicles by dialysis of nonionic alkyl maltoside detergents". Biochimica et Biophysica Acta (BBA) - Biomembranes. 946 (2): 379–388. doi:10.1016/0005-2736(88)90413-0. PMID   2850005.
3. Vanaken, T.; Foxall-Vanaken, S.; Castleman, S.; Ferguson-Miller, S. (1986). "Alkyl glycoside detergents: Synthesis and applications to the study of membrane proteins". Biomembranes Part M. Methods in Enzymology. Vol. 125. pp. 27–35. doi:10.1016/S0076-6879(86)25005-3. ISBN   9780121820251. PMID   3012259.
4. Strop, Pavel; Brunger, Axel T. (August 2005). "Refractive index-based determination of detergent concentration and its application to the study of membrane proteins". Protein Science. 14 (8): 2207–2211. doi:10.1110/ps.051543805. PMC   2279333 . PMID   16046633.