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.
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
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.