Undecyl-maltoside

Catalog Number	ACM253678670-1
CAS	253678-67-0
Structure
Synonyms	Undecyl-beta-D-maltoside
IUPAC Name	(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-(hydroxymethyl)-6-undecoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular Weight	496.6
Molecular Formula	C23H44O11
Canonical SMILES	CCCCCCCCCCCOC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O
InChI	InChI=1S/C23H44O11/c1-2-3-4-5-6-7-8-9-10-11-31-22-20(30)18(28)21(15(13-25)33-22)34-23-19(29)17(27)16(26)14(12-24)32-23/h14-30H,2-13H2,1H3/t14-,15-,16-,17+,18-,19-,20-,21-,22-,23-/m1/s1
InChI Key	UYEMNFYVTFDKRG-ZNGNCRBCSA-N
Purity	99%+
Complexity	539
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	10
Exact Mass	496.28836222
Heavy Atom Count	34
Hydrogen Bond Acceptor Count	11
Hydrogen Bond Donor Count	7
Isomeric SMILES	CCCCCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O
Monoisotopic Mass	496.28836222
Rotatable Bond Count	15
Topological Polar Surface Area	179 Ų

Knowledge & Learning Case Study Q&A

Undecyl-β-D-maltoside Used in the Purification of the Dimeric Cytochrome B6f Complex from Spinach and Maize

Zakharov SD, et al. Biophysical Journal, 2022, 121(2), 300-308.

Undecyl-β-D-Maltoside (UDM) is a nonionic detergent that plays a key role in the final stages of purification of the dimeric cytochrome b6f complex, facilitating detergent exchange and removing contaminants.
Methodology: The cytochrome b6f complex was initially extracted using a combination of octyl glucoside (OG) and sodium cholate detergents. Following extraction, insoluble materials were removed via centrifugation at 250,000 x g for 60 minutes. The supernatant was then treated with ammonium sulfate to 37.5% saturation and loaded onto a propyl-agarose column preequilibrated with a buffer containing UDM. This step allowed for extensive washing to remove green contaminants and facilitated the exchange of OG detergent to UDM. The complex was eluted using a buffer containing UDM and ammonium sulfate at 20% saturation.
The use of UDM in the purification process proved effective in exchanging detergents and removing green contaminants from the cytochrome b6f complex. Size-exclusion chromatography further purified the complex, yielding dimeric and monomeric b6f with high purity. The concentration of the purified complex was determined using spectrophotometry, and its electron transfer activity was confirmed through plastocyanin reduction assays.

Application of Undecyl-β-D-maltoside in the Purification of Monomeric Complex IV from Yeast Mitochondria.

Ing G, et al. Biochimica et Biophysica Acta (BBA) - Bioenergetics, 2022, 1863(7), 148591.

Undecyl-β-D-Maltoside (UDM), a non-ionic detergent, is employed in the solubilization and purification process to extract and stabilize the complex from mitochondrial membranes.
Methodology: Yeast strain W303-1B, genetically modified to incorporate a 6-histidine tag on the COX13 gene, was grown in YPGal medium and harvested during the late log phase. Mitochondrial membranes were prepared using differential centrifugation following mechanical disruption of cells. The membranes, with a total protein content of 2 mg/ml, were solubilized by incubation with 2% w/v UDM at 4°C for 1 hour. After centrifugation at 120,000 x g for 35 minutes to remove unsolubilized material, the supernatant was adjusted to pH 8.0 and loaded onto a Ni-NTA column pre-equilibrated with a buffer containing UDM. The column was washed, and complex IV was eluted with a buffer containing higher imidazole concentrations. The eluate was then supplemented with EDTA and ethylene glycol, flash-frozen, and stored at -80°C.
UDM proved effective in solubilizing mitochondrial membranes and stabilizing monomeric complex IV during purification. The process yielded a high-purity complex IV, suitable for further biochemical and structural analysis. The use of UDM ensured the integrity and activity of the complex, critical for studying its role in mitochondrial respiration.

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