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Merck

85990

Sigma-Aldrich

Succinyl-β-cyclodextrin

Sinónimos:

succ-β-CD, succinyl-β-CD

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About This Item

Número de CAS:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

form

powder

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Visite la Librería de documentos

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
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 Separations: Methods and Protocols
Methods in Molecular Biology (2004)
Hyunmyung Kim et al.
Chirality, 21(10), 937-942 (2009-02-11)
The chiral separation of (+/-)-catechin was investigated by capillary electrophoresis using characterized succinyl-beta-cyclodextrins (Suc-beta-CDs) with one to three degree of substitution values. The effects of nature and concentration of Suc-beta-CDs and running buffer pH on the migration time and resolution
Kwang-Woo Lee et al.
Journal of microbiology and biotechnology, 17(1), 74-80 (2007-12-07)
An enantioselective lipase gene (esf) for the kinetic resolution of optically active (S)-flurbiprofen was cloned from the new strain Serratia marcescens ES-2. The esf gene was composed of a 1,845-bp open reading frame encoding 614 amino acid residues with a

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