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) [3]
n-Dodecyl-β-D-maltopyranoside	DDM	0.17 [4]	510.6	~72 (~78-149 molecules) [5]
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. and Riek, R. (1998). "Reconstitution of Na+/K+-ATPase into phosphatidylcholine vesicles by dialysis of nonionic alkyl maltoside detergents" (PDF). Biochim. Biophys. Acta. 946 (2): 379–388. doi:10.1016/0005-2736(88)90413-0. PMID 2850005.{{cite journal}}: CS1 maint: multiple names: authors list (link)
https://www.anatrace.com/Products/Detergents/MALTOSIDES/D322LA.aspx
VanAken, T., Foxall-VanAken, S., Castleman, S. and 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.{{cite book}}: CS1 maint: multiple names: authors list (link)
Strop, P. and Brunger, A T. (2005). "Refractive index-based determination of detergent concentration and its application to the study of membrane proteins". Protein Sci. 14 (8): 2207–2211. doi:10.1110/ps.051543805. PMC 2279333. PMID 16046633.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[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. and Riek, R. (1998). "Reconstitution of Na+/K+-ATPase into phosphatidylcholine vesicles by dialysis of nonionic alkyl maltoside detergents" (PDF). Biochim. Biophys. Acta. 946 (2): 379–388. doi:10.1016/0005-2736(88)90413-0. PMID 2850005.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] ttps://www.anatrace.com/Products/Detergents/MALTOSIDES/D322LA.aspx

[4] VanAken, T., Foxall-VanAken, S., Castleman, S. and 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.{{cite book}}: CS1 maint: multiple names: authors list (link)

[5] Strop, P. and Brunger, A T. (2005). "Refractive index-based determination of detergent concentration and its application to the study of membrane proteins". Protein Sci. 14 (8): 2207–2211. doi:10.1110/ps.051543805. PMC 2279333. PMID 16046633.{{cite journal}}: CS1 maint: multiple names: authors list (link)