Search results for "Glycosidic bond"
showing 10 items of 20 documents
Characterization of the trimeric, self-recognizing Geodia cydonium lectin I.
1983
A D-galactose-specific lectin I was extracted from the sponge Geodia cydonium and purified by affinity chromatography. The molecular weight of lectin I as determined by high-pressure liquid gel chromatography, was found to be 36500 +/- 1300. Disc gel electrophoresis in the presence and in the absence of sodium dodecyl sulfate showed that lectin I is a trimer composed of three different subunits (Mr: 13800, 13000 and 12200); two of the three subunits are linked by one disulfide bond. Isoelectric focusing gave a pI of 5.6 for the native molecule and a pI of 4.4 and of 7.4 for the subunits. The three subunits carry carbohydrate side chains, composed of D-galactose (94%) and of arabinose (5%). …
A new neuraminic acid derivative and three types of glycopeptides isolated from the Cuvierian tubules of the sea cucumber Holothuria forskali
1973
The Cuvierian tubules of Holothuria forskali Della Chiaje, a sea cucumber found in the Adriatic Sea, were investigated with regard to their carbohydrate moieties. From a Pronase digest of these tubules three types of carbohydrate units were isolated and characterized. 1. A high-molecular-weight glycopeptide fraction was shown to contain sulphated polyfucose, galactosamine, a uronic acid and a previously unknown neuraminic acid derivative. The sulphate was shown by i.r. analysis to be present as an O-ester. The carbohydrate unit was linked O-glycosidically to threonine and serine residues in the polypeptide chain. The hitherto unknown neuraminic acid derivative (Hf-neuraminic acid) was resis…
Glycosylated macromolecular conjugates of antiviral drugs with a polyaspartamide.
2004
Two new polymeric conjugates for specific liver targeting were prepared by conjugation of sugar moieties and antiviral drugs to alpha, beta-poly[N-2-(hydroxyethyl)-DL-aspartamide] (PHEA). PHEA-galactopyranosylphenylthiocarbamide-mono-O-succinylganciclovir (conjugate 7) and PHEA-mannopyranosylphenylthiocarbamide-O-succinylacyclovir (conjugate 8) were synthesized according to a multi-step procedure which allowed for obtaining high product yield and process standardization. Conjugate 7 contained 7.5 and 8.5% of galactose and ganciclovir (substituent/repeating unit, mol/mol), respectively, and conjugate 8 contained 14.2 and 10.8% of mannose and acyclovir, respectively. In vitro studies demonstr…
Glycosidic juvenogens: derivatives bearing alpha,beta-unsaturated ester functionalities.
2007
Abstract A series of the protected alkyl glycosides 5a / 5b – 12a / 12b was synthesized from the parent isomeric alcohols (insect juvenile hormone bioanalogs; juvenoids), 4-[4′-(2″-hydroxycyclohexyl)methylphenoxy]-3-methyl-but-2-enoic acid ethyl ester ( 1a / 1b – 4a / 4b ; racemic structures) and ( 1a – 4a ; enantiopure structures). Cadmium carbonate was used as a promoter of this Koenigs–Knorr reaction, and the products were obtained in 82–92% yields. Deprotection of the carbohydrate functionality of 5a / 5b – 12a / 12b was carefully performed using ethanolysis in the presence of zinc acetate, due to the presence of another ester functionality in the aglycone part of the molecule of protec…
Hederagenin glycosides from the fruits of Blighia unijugata
2019
Abstract A phytochemical investigation of Blighia unijugata led to the isolation of eleven hederagenin glycosides. Among these compounds, six are previously undescribed, two are described in their native forms for the first time and three are known whereas firstly isolated from Blighia unijugata. The structure of the undescribed compounds was elucidated on the basis of 2D NMR and mass spectrometry analyses as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyr…
Palladium-Catalyzed C—C Coupling Reactions in the Enantioselective Synthesis of 2,4-Disubstituted 4,5-Dehydropiperidines Using Galactosylamine as a S…
2005
Abstract Stereoselective synthesis of enantiomerically pure 2,4-disubstituted piperidine derivatives, which are considered interesting pharmacophoric structures, was achieved starting with a tandem Mannich–Michael reaction sequence on O -pivaloylated N -galactosyl aldimines. Subsequent conversion of the thus formed 2-substituted dehydropiperidinones into the corresponding enol triflates was carried out by conjugate hydride addition and trapping the enolate with N , N -bis(trifluoromethanesulfonyl)aniline. Their Suzuki–Miyaura coupling with aryl and heteroaryl boronic acids was performed under conditions compatible with the carbohydrate structure, in particular, with the sensitive N -glycosi…
A truncated driven Overhauser effect study of Adriamycin in water: Conformation of the glycosidic linkage
1991
Abstract Truncated driven nuclear Overhauser effect difference spectra have been used to ascertain the conformational characteristics of the glycosidic linkage of Adriamycin in aqueous solution. The “two-spin approximation” has been employed to evaluate the cross-relaxation rates between nearby protons and to obtain the relative internuclear distances. The rotational angles φ1 = C(7)−O(7)−C(1′)−(H1′) and φ2 = H(7)−C(7)−O(7)−C(1′) have also been calculated.
Synthesis of active principles from the leaves of Moringa oleifera using S-pent-4-enyl thioglycosides
1998
Abstract α - l -Rhamnosides of 4-hydroxy-benzyl compounds with nitrile, carbamate, and thiocarbamate groups occurring in Moringa oleifera leaf extracts and the α - l -rhamnoside of anisaldehyde derivatives were synthesised. Electrophilic activation of S -pent-4-enyl thiorhamnosides was applied for the construction of glycosidic linkages.
ChemInform Abstract: Synthesis of Active Principles from the Leaves of Moringa oleifera Using S-Pent-4-enyl Thioglycosides.
2010
Abstract α - l -Rhamnosides of 4-hydroxy-benzyl compounds with nitrile, carbamate, and thiocarbamate groups occurring in Moringa oleifera leaf extracts and the α - l -rhamnoside of anisaldehyde derivatives were synthesised. Electrophilic activation of S -pent-4-enyl thiorhamnosides was applied for the construction of glycosidic linkages.
Water-induced local ordering of chitosan polymer chains in thin layer films
2015
International audience; Carbon-13 NMR (CP-MAS and FSLG 1H–13C HETCOR) have been applied to chitosan salt films synthesized in acetic acid and exposed to different relative humidity environments (32% or 75%) at 20 °C for 1 month. It gives insight in the relationship between structure and functional properties according to the hydration level of this biomaterial as a film. The acetate ions trapped in the chitosan act as structuring agents between chitosan chains for the low hydration state. But, increasing the moisture content induces spontaneous removal of acetic acid and a subsequent modification in the film structure, with an increase in local ordering. HETCOR experiments also showed a mul…