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Sigma-Aldrich

Succinyl-β-cyclodextrin

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Synonym(s):
succ-β-CD, succinyl-β-CD
MDL number:
MFCD00800297
PubChem Substance ID:
57653074
NACRES:
NA.25

form

powder

Quality Level

100

impurities

~5% water

color

white

mp

225  °C ((437 °F ) - Decomposes on heating)

storage temp.

−20°C

SMILES string

CC(=O)CCC(=O)OC[C@H]1O[C@@H]2O[C@H]3[C@@H](O)[C@H](O)[C@H](O[C@@H]3COC(=O)CCC(O)=O)O[C@H]4[C@@H](O)[C@H](O)[C@H](O[C@@H]4COC(=O)CCC(O)=O)O[C@H]5[C@@H](O)[C@H](O)[C@H](O[C@@H]5COC(=O)CCC(O)=O)O[C@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]6COC(=O)CCC(O)=O)O[C@H]7[C@@H](O)[C@H](O)[C@H](O[C@@H]7COC(=O)CCC(O)=O)O[C@H]8[C@@H](O)[C@H](O)[C@H](O[C@@H]8COC(=O)CCC(O)=O)O[C@H]1[C@@H](O)[C@@H]2O

InChI

1S/C71H100O55/c1-23(72)2-9-37(85)106-16-24-58-44(92)51(99)65(113-24)121-59-25(17-107-38(86)10-3-31(73)74)115-67(53(101)46(59)94)123-61-27(19-109-40(88)12-5-33(77)78)117-69(55(103)48(61)96)125-63-29(21-111-42(90)14-7-35(81)82)119-71(57(105)50(63)98)126-64-30(22-112-43(91)15-8-36(83)84)118-70(56(104)49(64)97)124-62-28(20-110-41(89)13-6-34(79)80)116-68(54(102)47(62)95)122-60-26(18-108-39(87)11-4-32(75)76)114-66(120-58)52(100)45(60)93/h24-30,44-71,92-105H,2-22H2,1H3,(H,73,74)(H,75,76)(H,77,78)(H,79,80)(H,81,82)(H,83,84)/t24-,25-,26-,27-,28-,29-,30-,44+,45+,46+,47+,48+,49+,50+,51+,52+,53+,54+,55+,56+,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-/m1/s1

InChI key

DIRLEDPEXJLCIL-JCWBWLHSSA-N

Related Categories

General description

Succinyl-β-cyclodextrin is a negatively charged cyclodextrin derivative that has major implications in the chiral separation of neutral and basic analytes by means of capillary electrophoresis (CE), owing to its counter-current mobility.

Application

Cyclodextrins (CD) are cyclic oligosaccharides composed of D-glucose units connected via α(1→4) glycosidic bonds. Common cyclodextrins contain six (α-CD); seven (β-CD) or eight (gamma-CD) D-glucose units. Cyclodextrins are sometimes derivitized through esterification at positions two, three and/or six.
Succinyl-β-cyclodextrin and carboxymethyl-β-cyclodextrin are used as chiral selective agents in capillary electrophoresis for the separation of di- and tri-peptide enantiomers and catechin enantiomers. Succinyl-β-cyclodextrin is used to optimize analysis of PNA-DNA duplexes with diethylthiadicarbocyanine dye.
Succinyl-β-cyclodextrin may be used as a chiral selector to resolve:
  • Acylamine fungicides in commercial agrochemical formulations by electrokinetic chromatography (EKC).
  • Catechin isomers in human biological samples and antihistamines in pharmaceutical preparations by CE.

Other Notes

To gain a comprehensive understanding of our extensive range of Polysaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Chiral Separations: Methods and Protocols
Methods in Molecular Biology (2004)
S Sabbah et al.
Electrophoresis, 22(7), 1385-1393 (2001-05-31)
The separation of the LL and DD enantiomers of dipeptides and tripeptides using cyclodextrins (CDs) containing carboxyl groups was investigated with respect to the amino acid sequence of the peptides, the nature of the cyclodextrin and the buffer pH. Compared
Influence of methanol on the enantioresolution of antihistamines with carboxymethyl-beta-cyclodextrin in capillary electrophoresis
Van Eeckhaut A, et al.
Electrophoresis, 25(16), 2838-2847 (2004)
Chiral separation of agricultural fungicides
Perez-Fernandez V, et al.
Journal of Chromatography A, 1218(38), 6561-6582 (2011)
Tullia Tedeschi et al.
Journal of biochemical and biophysical methods, 70(5), 735-741 (2007-05-26)
The 3,3'-diethylthiacarbocyanine (DiSC(2)(5)) dye is able to aggregate on full matched PNA-DNA duplexes by changing its absorption properties, which are manifested by an instantaneous colour shift from blue to purple. However the spontaneous aggregation of the dye also on mismatched
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