Synthesis of Cyclodextrin Derivatives Carrying Bio-Recognisable Saccharide Antennae

Kassab, Rima; Félix, C.; Parrot‐Lopez, Hélène; Bonaly, R.

doi:10.1016/s0040-4039(97)10033-8

Cited by 41 publications

(27 citation statements)

References 6 publications

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“…1 Starting Materials. The pseudothioureas derivatives 4-6 were obtained from the corresponding halides 1-3 according to the procedures described by Horton et al 40,41 Acetylated 1-thio-R-D-mannose 8 was obtained from acetobromomannose 7 following the procedure described by Matta et al 39 Compounds 9 and 12 were obtained following the method described by Monsigny et al 46 Heptakis(6-deoxy-6-iodo)cyclomaltoheptaose 13 was obtained following the method described by Gadelle et al 47 following the method described by Ashton et al 44 Chloroacetic anhydride (technical grade 90%) and N-tert-butoxycarbonyl-1,6-hexamethylenediamine hydrochloride (35) were purchased from Aldrich. The lectins from Canavalia ensiformis (concanavalin A, Con A) and Triticum vulgaris (wheat germ, WGA) were purchased from Sigma (cat.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Per-Glycosylated β-Cyclodextrins Having Enhanced Lectin Binding Affinity

et al. 1998

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A cyclomaltooligosaccharide containing seven R-(1f4)-D-glucopyranosyl units ( -cyclodextrins) was transformed into heptakis 6-deoxy-6-iodo (13) and heptakis 6-amino-6-deoxy (25) derivatives using known procedures. Compound 13 was peracetylated and condensed in one pot with the known peracetylated pseudothiouronium salts of -D-glucopyranose (4), -D-galactopyranose (5), or -D-N-acetylglucopyranosylsamine (6) or with R-D-1-deoxy-1-thiomannopyranose (8) using cesium carbonate in dimethylformamide. Alternatively, peracetylated 4-aminophenyl-R-D-mannopyranoside (9) was transformed into either extended pseudothiouronium 11 following N-chloroacetylation and nucleophilic substitution by thiourea or into 4-isothiocyanatophenyl R-D-mannopyranoside 12 using thiophosgene. Each of the four thiolated sugar derivatives 4-6 or 8 were also coupled to heptakis chloroacetamido -CD 26 obtained from heptakis amine 25 after N-chloroacetylation. Further incorporation of a hexamethylenediamine spacer arm onto heptakis iodo -CD 13 using thiol derived from mono-Boc derivative 36 and coupling to isothiocyanate 12 after suitable deprotection afforded permannosylated derivative 38. Zemplén de-O-acetylation of all -CD derivatives provided watersoluble persubstituted compounds containing D-glucopyranosides (18, 30), D-galactopyranosides (19, 31), D-N-acetylglucosaminides (20, 32), and D-mannopyranosides (22, 24, 34, 39), respectively. The compounds were then evaluated for their relative binding properties toward natural carbohydrate binding plant lectins using both microtiter plate competitive inhibition experiments, double sandwich assays using horseradish peroxidase labeled lectins and by turbidimetric assays. The plant lectins from Pisum sativum (pea), Arachis hypogea (peanut), Canavalia ensiformis (Concanavalin A), and Triticum vulgaris (WGA, wheat germ agglutinin) were used for -D-glucose, -D-galactose, R-Dmannose, and -D-N-acetylglucosamine, respectively. All persubstituted -CDs showed good to excellent inhibitory properties together with abilities to cross-link their analogous plant lectins. The capacity of perglycosylated -CDs to anchor both microtiter plate-coated lectins and their corresponding peroxidase-labeled derivatives further confirmed the usefulness of these multivalent neoglycoconjugates in bioanalytical assays.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Per-Glycosylated β-Cyclodextrins Having Enhanced Lectin Binding Affinity

et al. 1998

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“…2 In the present study, we have determined the crystal structures of the 2,3,4,6-tetra-O-acetyl-p-D-galactopyranosyl isothiocyanate (1) and of the 2,3,4,6-tetra-O-acetylp-D-galactopyranosyl azide (2). The structure determination of compound 1, is the first structural characterization of a pyranosyl isothiocyanate.…”

Section: Introductionmentioning

confidence: 94%

“…They have been widely used as key intermediates in the chemical synthesis of N-glycopeptides 1 and N-glycoconjugates. 2 The corresponding iV-glycosidic linkage is obtained by easy conversion of glycosyl 1019 Copyright © 1999 by Marcel Dekker, Inc.…”

Section: Introductionmentioning

confidence: 99%

Comparative X-Ray Single Crystal Study of Acetylated-β-D-Galactopyranosyls Azide and Isothiocyanate

Selkti

Kassab

Lopez

et al. 1999

Journal of Carbohydrate Chemistry

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The structures of two peracetylated p-D-galactopyranosides substituted at the anomeric C atom with either an isothiocyanate or an azide group, have been determined by single crystal X-ray diffraction analysis. The two compounds show very similar molecular conformation, except for the substituent groups at the anomeric C atom and for the acetyl groups of the 0 6 atoms. They crystallize in different infinite chain-type structures. While the isothiocyanate group extends in a large intermolecular space, the azide group is placed in a more crowded environment.

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“…A lot of molecular recognition investigation has been reported so far. At present, the molecular recognition by b-CD focuses on fullerene [5,6], carbohydrates [7,8], polymer [9][10][11][12] and ternary inclusion complexes [13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Molecular recognition of naphthalenediamine by polyamine modified β-cyclodextrin:yttrium metal complexes

Jiang

Yang

Zhang

2011

J Incl Phenom Macrocycl Chem

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The 6-OH group of b-cyclodextrin was modified by diethylene triamine and triethylene tetramine, respectively, mono[6-diethylenetriamino]-6-deoxy-b-cyclo dextrin (DTCD) and mono[6-triethylenetetraamino]-6-deoxy-b-cyclodextrin (TTCD) were synthesized, which included 1,5-naphthalenediamine and 1,8-naphthalenediamine, respectively, in the presence of rare earth metal yttrium chloride. As a result, four ternary inclusion complexes (host-guest-metal) formed, which were characterized via 1 HNMR spectroscopy. The chemical shift variations of host and guest molecules were studied. The stoichiometric proportion of host and guest molecules is 2:1 for all the complexes. Signal degeneration still exists for the guest molecules after the inclusion process, which verifies the symmetrical conformation of guest molecules inside the cavities of two host molecules. All the four complexes exhibit ''sandwich''-typed structure.

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Synthesis of Cyclodextrin Derivatives Carrying Bio-Recognisable Saccharide Antennae

Cited by 41 publications

References 6 publications

Synthesis of Per-Glycosylated β-Cyclodextrins Having Enhanced Lectin Binding Affinity

Synthesis of Per-Glycosylated β-Cyclodextrins Having Enhanced Lectin Binding Affinity

Comparative X-Ray Single Crystal Study of Acetylated-β-D-Galactopyranosyls Azide and Isothiocyanate

Molecular recognition of naphthalenediamine by polyamine modified β-cyclodextrin:yttrium metal complexes

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