Lecithin organogels with n-alkyl-D- glucosides and n-alkly-D-lactobionamide

 Jelly-like phases formed by mixtures of soybean lecithin with pure n-dodecyl-β-D-glucopyranoside (DDPG), commercial alkylpoly-glucoside (APG) or n-dodecyl-β-D-lactobionamide (DLBA) in decane in the presence of small amounts of water were studied by oscillating rheology and FT-IR-spectroscopy. It was established that the sugar derivatives can modify the rheological properties of lecithin organogels in different ways. The viscosities, the structural relaxation times and the shear moduli decrease with increasing content of DDPG, while the same parameters increase for DLBA. For APG the modulus is increasing while the viscosity and the structural relaxation time are decreasing. By means of FT-IR spectroscopy and examination of the Cole–Cole-plots of the loss modulus vs. the storage modulus it was shown that the sugar derivatives influence both the strength of the hydrogen bonds between the molecules in the polymer-like micelles and the micellar dynamics. Received: 10 November 1997 Accepted: 11 December 1997     

Synthesis of oligosaccharides related to the HNK-1 antigen. 5. Synthesis of a sulfo-mimetic of the HNK-1 antigenic trisaccharide

2-Aminoethyl 3,6-di-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside, which is the sulfo-mimetic of the antigenic trisaccharide HNK-1, and the corresponding monosulfates, viz., 2-aminoethyl 3-O-sulfo-and 2-aminoethyl 6-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→ 4)-2-acetamido-2-deoxy-β-D-glucopyranosides, were synthesized. 2-Azidoethyl 2,4-di-O-benzoyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1→ 4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside served as the common precursor for the sulfated trisaccharides. This compound was synthesized according to the [2+1] pattern from monosaccharidic precursors: 3,6-di-O-acetyl-2,4-di-O-benzoyl-D-glucopyranosyl trichloroacetimidate, allyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside, and 2-azidoethyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside. The structures of the glycosyl donors and glycosylation conditions were optimized for the efficient synthesis of the glucosyl-β-(1→3)-galactose disaccharide block and its subsequent transformation into the target trisaccharide sequence. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1593–1607, August, 2007.     

Mild Pfitzner—Moffat oxidation of the (1→3)-β-D-glucan from Saccharomyces cerevisiae

The structure of the cell wall glucan isolated from the industrial strain of Saccharomyces cerevisiae was characterized as to be composed of a linear (1→3)-β-D-glucan chain with single β-D-glucopyranosyl residues attached to every ninth backbone unit by (1→6)-glycosidic linkages. Mild oxidation of this β-D-glucan with a dimethyl sulfoxide—acetic anhydride reagent yielded an “oxidized” glucan with aldehyde groups introduced at C-6 and carbonyl oxygens located at C-2 and C-4 of the glucopyranosyl rings. The conversion of the oxidized glucan into the polyoxime was used to study the progress of oxidation and to establish the carbonyl groups distribution in this new reactive polysaccharide derived from baker’s yeast cell wall.     

Polar steroidal compounds from the Far-Eastern starfish <Emphasis Type="Italic">Lethasterias fusca</Emphasis>

Nine steroidal compounds including three new steroidal glycosides, viz., sodium (24S)-3,24-di-O-(β-D-xylopyranosyl)-5α-cholestane-3β,6β,8,15α,24-pentol 15-sulfate (fuscaside A), (24S)-3,24-di-O-(β-D-xylopyranosyl)-5α-cholestane-3β,6β,8,15α,24-pentol (fuscaside B), and (22E,24R)-24-O-(β-D-xylopyranosyl)-5α-cholest-22-ene-3β,6α,8,15β,24-pentol (desulfated minutoside A); three previously known glycosides, viz., distolasterosides D₁ and D₂ and pycno-podioside A; two previously known polyhydroxysteroids, viz., 5α-cholestane-3β,6α,8,15β,16β,26-hexaol and 5α-cholestan-3β,4β,6α,7⇇8,15β,16β,26-octol; and the known sodium 24,25-dihydro-marthasterone 3-sulfate were isolated from the Far-Eastern starfish Lethasterias fusca. The structures of these compounds were elucidated by NMR spectroscopy and mass spectrometry. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 196–200, January, 2008.     

Comparison and characterization of polysaccharides from natural and cultured <Emphasis Type="Italic">Cordyceps</Emphasis> using saccharide mapping

Comparison and characterization of polysaccharides from natural and cultured Cordyceps on the basis of their chemical characteristics such as glycosidic linkages were performed for the first time using saccharide mapping. The results showed that polysaccharides from most of the natural and cultured Cordyceps had similar responses to enzymatic digestion. These polysaccharides mainly contained (1→4)-β-D-glucosidic linkages, and (1→4)-α-glucosidic, (1→6)-α-glucosidic, 1,4-β-D-mannosidic, as well as (1→4)-α-D-galactosiduronic linkages also existed in some polysaccharides. Especially, natural and cultured Cordyceps polysaccharides could be discriminated on the basis of high performance liquid chromatography profiles of pectinase hydrolysates, which is helpful to control the quality of polysaccharides from Cordyceps.     

New polyhydroxysteroids and steroid glycosides from the far east starfishCeramaster patagonicus

Two new polyhydroxysteroids and five new glycosides were isolated from the starfishCeramaster patagonicus and their structures were elucidated: 5α-cholestane-3β,6α,15β,16β,26-pentol, (22E)-5α-cholest-22-ene-3β,6α,8,15α,24-pentol, (22E)-28-O-[O-(2-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-hydroxymethyl-5α-cholest-22-ene-3β,4β, 6α,8,15β,16β,28-heptol (ceramasteroside C₁), (22E)-28-O-[O-(2,4-di-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-hydroxymethyl-5α-cholest-22-ene-3β, 6α,8,15β,16β,28-hexol (ceramasteroside C₂), (22E)-28-O-[O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-hydroxymethyl-5α-cholest-22-ene-3β,6α,8,15β,16β 28-hexol (eramasteroside C₃), (22E)-28-O-[O-(2-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-methyl-5α-cholest-22-ene-3β,4β,6α,8, 15β, 26-hexol (ceramasteroside C₄), and (22E)-28-O-[O-(2-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-xylopyranosyl]-5α-cholest-22-ene-3β,6α,8,15β,24-pentol (ceramasteroside C₅)). Three known polyhydroxysteroids (24-methylene-5α-cholestane-3β,6α,8,15β,16β,26-hexol, 5α-cholestane-3β,6α,8,15β,16β,26-hexol, and 5α-cholestane-3β,6β,15α,16β,26-pentol) were also isolated. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 190–195, January, 1997.     

Selenium metabolites in human urine after ingestion of selenite, <Emphasis Type="SmallCaps">L</Emphasis>-selenomethionine,or <Emphasis Type="SmallCaps">DL</Emphasis>-selenomethionine: a quantitative case study by HPLC/ICPMS

To obtain quantitative information on human metabolism of selenium, we have performed selenium speciation analysis by HPLC/ICPMS on samples of human urine from one volunteer over a 48-hour period after ingestion of selenium (1.0 mg) as sodium selenite, L-selenomethionine, or DL-selenomethionine. The three separate experiments were performed in duplicate. Normal background urine from the volunteer contained total selenium concentrations of 8–30 μg Se/L (n=22) but, depending on the chromatographic conditions, only about 30–70% could be quantified by HPLC/ICPMS. The major species in background urine were two selenosugars, namely methyl-2-acetamido-2-deoxy-1-seleno-β-D-galactopyranoside (selenosugar 1) and its deacylated analog methyl-2-amino-2-deoxy-1-seleno-β-D-galactopyranoside (selenosugar 3). Selenium was rapidly excreted after ingestion of the selenium compounds: the peak concentrations (∼250–400 μg Se/L, normalized concentrations) were recorded within 5–9 hours, and concentrations had returned to close to background levels within 48 hours, by which time 25–40% of the ingested selenium, depending on the species ingested, had been accounted for in the urine. In all experiments, the major metabolite was selenosugar 1, constituting either ∼80% of the total selenium excreted over the first 24 hours after ingestion of selenite or L-selenomethionine or ∼65% after ingestion of DL-selenomethionine. Selenite was not present at significant levels (<1 μg Se/L) in any of the samples; selenomethionine was present in only trace amounts (∼1 μg/L, equivalent to less than 0.5% of the total Se) following ingestion of L-selenomethionine, but it constituted about 20% of the excreted selenium (first 24 hours) after ingestion of DL-selenomethionine, presumably because the D form was not efficiently metabolized. Trimethylselenonium ion, a commonly reported urine metabolite, could not be detected (<1 μg/L) in the urine samples after ingestion of selenite or selenomethionine. Cytotoxicity studies on selenosugar 1 and its glucosamine isomer (selenosugar 2, methyl-2-acetamido-2-deoxy-1-seleno-β-D-glucosopyranoside) were performed with HepG2 cells derived from human hepatocarcinoma, and these showed that both compounds had low toxicity (about 1000-fold less toxic than sodium selenite). The results support earlier studies showing that selenosugar 1 is the major urinary metabolite after increased selenium intake, and they suggest that previously accepted pathways for human metabolism of selenium involving trimethylselenonium ion as the excretionary end product may need to be re-evaluated.     

Synthesis of saccharide precursors for preparation of potential inhibitors of glycosyltranferases

Ethyl 6-O-tert-butyldimethylsilyl-3,4-di-O-acetyl-2-thio-α-D-fructofuranoside (Va), its β-analog (Vb); as well as benzyl 6-O-tert-butyldimethylsilyl-3,4-di-O-acetyl-2-thio-α-D-fructofuranoside (Xa) and its β-analog (Xb), having an unprotected OH group at C-1, were prepared by sequential synthesis starting from commercially available D-fructose. These compounds represent suitable nucleophiles for the preparation of model carbohydrate mimetics of a glycosyltransferase inhibitor type in transition state. The structures of all compounds were confirmed by NMR spectral data and elemental analyses.     

Synthesis of bis(glycosylamino)alkanes and bis(glycosylamino)arenes

The condensation of D-mannose and D-galactose with aliphatic and aromatic diamines afforded a series of bis(glycosylamino)alkanes and-arenes. A possible mechanism was proposed for the formation of 1,2-bis(β-D-glycosylamino)benzenes. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2793–2801, December, 2005.     

Surface adsorption and micelle formation of aqueous solutions of polyethyleneglycol and sugar surfactants

The surface tension of aqueous solutions of tetraethyleneglycol octyl ether (C8E4) and octyl-β-d-maltopyranoside (OM) mixture was measured as a function of the total molality of surfactants and the composition of OM under atmospheric pressure at 298.15 K by drop volume technique. The results of surface tension measurements were analyzed by originally developed thermodynamic equations, then phase diagrams of adsorption and micelle formation were constructed. From the analysis of the surface tension data, it was found that the C8E4 and OM molecules interact attractively in the adsorbed film and the excess Gibbs energy of adsorption can be compared with those observed in typical cationic–nonionic surfactant systems; nevertheless, they are mixed almost ideally in the mixed micelle. Judging from a negative excess surface area calculated by differentiating the excess Gibbs energy by the surface tension, we concluded that the attraction between C8E4 and OM molecules is a short-range one originated in the hydrogen bonding between them which favors the planar configuration.     

Stereochemical aspects of micellar properties of esterified glucoside surfactants in water: apparent molar volume, adiabatic compressibility, and aggregation number

 The apparent molar volume and the apparent molar adiabatic compressibility of the sugar-based surfactants methyl 6-O-octanoyl-α-d-glucopyranoside (α-MOnG), methyl 6-O-octanoyl-β-d-glucopyranoside (β-MOnG), and octyl β-d-glucoside were measured over a wide concentration range. Also, the aggregation number of their micelles was determined from the Debye plot using static light scattering data. It was found that the micellar aggregation number for α-MOnG is 179 at 35 °C, which is 1.5 times larger than that for β-MOnG, suggesting that the anomerism of the head group influences the packing of the monomers during micelle formation. Received: 30 September 1999 Accepted: 15 December 1999     

Determination and Pharmacokinetic Study of Calycosin-7-O-β-d-glucoside in Rat Plasma After Intravenous Administration of Aidi Lyophilizer

Aidi injection is a clinical medicine used in China for the treatment of cancer. Calycosin-7-O-β-d-glucoside is the main effective components of the formulas. In this study, a high performance liquid chromatographic (LC) method was developed to quantify calycosin-7-O-β-d-glucoside in rat plasma using a liquid–liquid extraction and ultraviolet (UV) absorbance detection. LC analysis was performed on a Diamonsil C₁₈ column (200 × 4.6 mm i.d., 5 μm particle size) with isocratic mobile phase consisting of acetonitrile–0.05% phosphoric acid (19.5:80.5, v/v) of a flow rate of 1.0 mL min⁻¹. The linear range was 0.11–17.6 μg mL⁻¹ and the low quantification limit was 0.11 μg mL⁻¹ (S/N = 10). The intra- and inter-day relative standard deviations (RSD) in the measurement of quality control (QC) samples 0.11, 0.22, 1.32 and 8.80 μg mL⁻¹ ranged from 4.1 to 6.3 and 4.3 to 6.2%, respectively. The accuracy was from −6.7 to 4.3% in terms of relative error (RE). Calycosin-7-O-β-d-glucoside was stable in storage at −20 °C for 2 weeks and stable after three freeze–thaw cycles in rat plasma. This method was validated for specificity, accuracy, precision and was successfully applied to pharmacokinetic study of calycosin-7-O-β-d-glucoside in rat plasma after intravenous administration of Aidi lyophilizer.     

Four new steroid glycosides from the Vietnamese starfish <Emphasis Type="Italic">Linckia laevigata</Emphasis>

Eighteen steroid compounds, including four new steroid glycosides, viz., linckosides L3–L6, along with the previously known nine glycosides and five free polyhydroxysteroids, were isolated from the starfish Linckia laevigata collected on the Vietnamese coast. New compounds contain the 2-O-methyl-β-D-xylopyranosyl unit at the C(3) atom of polyhydroxylated steroidal aglycone. Two of these compounds are monosides, and the other two belong to biosides and have an additional β-D-xylopyranosyl residue at C(26) in the side chain of the aglycone. The structures of the new compounds were determined by NMR spectroscopy, mainly by 2D NMR, and mass spectrometry. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 792–799, April, 2007.     

ABA- and BAB-triblock cooligomers of tri-<Emphasis Type="Italic">O</Emphasis>-methylated and unmodified cello-oligosaccharides: syntheses and structure-solubility relationship

Triblock cooligomers consisting of tri-O-methyl-glucopyranosyl and unmodified glucopyranosyl residues, methyl 2,3,4,6-tetra-O-methyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-α-d-glucopyranoside (1: ABA triblock cooligomer; DS = 2.1) and β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-d-glucopyranose (2: BAB triblock cooligomer; DS = 1.8) were prepared. Compound 1 dissolved both in distilled water and chloroform but compound 2 dissolved in distilled water not in chloroform, though compounds 1 and 2 consist of 4 tri-O-methyl-glucopyranosyl and 2 unmodified anhydro glucopyranosyl units.     

New class of carbohydrate-based nonionic surfactants: diblock co-oligomers of tri-<Emphasis Type="Italic">O</Emphasis>-methylated and unmodified cello-oligosaccharides

Mixtures of diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides have been found to be amphiphilic, as reported before. In order to clarify their accurate amphiphilic property, diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides with monodispersity, methyl β-d-glucopyranosyl-(1→4)-2,3,6–tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6–tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-d-glucopyranoside (1, pentamer), methyl β-d-glucopyranosyl-(1→4)- β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-d-glucopyranoside (2, hexamer), and methyl β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)- 2,3,6-tri-O-methyl-d-glucopyranoside (3, trimer) were synthesized independently. These compounds had higher surface activities compared to the mixture of diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides and commercially available methylcellulose (MC) SM-4. This paper describes the methods of synthesis of these compounds, and the influence of amphiphilic character on their surface activity. A new class of carbohydrate-based nonionic surfactant without long alkyl chain was discovered.     

Synthesis of blockwise alkylated tetrasaccharide–organic quantum dot complexes and their utilization for live cell labeling with low cytotoxicity

Bioimaging is a key to understanding immune responses, cell differentiation, and development. Quantum dots (QDs) conjugated with monoclonal antibodies and other biomolecules are currently utilized for flow cytometry and immunohistochemistry, but monoclonal antibody–QD complexes are of limited use when cell surface markers are not available. In this study, we synthesized novel amphiphilic blockwise alkylated tetrasaccharides and developed a simple method for labeling a wide variety of live cells with organic QDs encapsulated with these carbohydrates. The novel amphiphilic blockwise alkylated tetrasaccharides were as follows: methyl β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-d-glucopyranoside (1), methyl β-d-galactopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-methyl-d-glucopyranoside (2), ethyl β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-ethyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-ethyl-d-glucopyranoside, (3), and ethyl β-d-galactopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-ethyl-β-d-glucopyranosyl-(1 → 4)-2,3,6-tri-O-ethyl-d-glucopyranoside (4). The newly synthesized blockwise alkylated tetrasaccharides spontaneously assembled into micelle-like particles, in which the hydrophobic moiety of the blockwise alkylated tetrasaccharides played an important role. They were less toxic to human cells than octyl β-d-glucopyranoside, a commonly used amphiphilic glucoside. Flow cytometry and confocal laser scanning microscopy revealed that the blockwise alkylated tetrasaccharide–organic QD complexes were stably attached to live cells. The affinity of compounds 1 and 2 to the live cell surface was slightly higher than that of compounds 3 and 4. Because the preparation of these carbohydrate–QD complexes is simple and does not require sophisticated equipment, and because the complexes can be autonomously attached to a wide spectrum of cell lines, they can be used as cell labeling reagents in biomedical studies.     

Stereoselective synthesis of triterpene 2-deoxy-α-d-lyxo-hexopyranosides

2-Deoxy-α-d-lyxo-hexopyranosides of 18β-glycyrrhetic acid, its 11-deoxo derivative and allobetulin were synthesized by glycosylation of oleonane-type triterpene alcohols withd-galactal acetate in the presence ofN-iodosuccinimide followed by deiodination and deprotection. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 596–600. March, 1997.     

Structural and calorimetric investigations on nonaqueous liquid crystals and gel phases in the binary system K-stearate/glycerol

The K-stearate/glycerol (KC₁₈/Gl) binary system was studied at mole fractions of stearate of x _KC18 = 0.10, 0.25, 0.30 and 0.50. Small- and wide-angle X-ray diffraction (XRD) measurements were combined with differential scanning calorimetry (DSC) measurements at different temperatures. The investigations were intended to verify the previously published phase diagram and were targeted at the confirmation of the gel-like (G₁) phase and the isotropic (I) phase. The XRD and DSC measurements lead to the conclusion that the G₁ phase as well as the I phase, the existence of which had been proposed from texture observations, do in fact not exist. Consequently, a correction of the preliminary phase diagram is given. This corrected phase diagram reveals the crystalline phase (C) ⇆ gel phase (G) ⇆ hexagonal phase (H_α) ⇆ isotropic, micellar phase phase transitions for low KC₁₈ concentrations of x _KC18 = 0.15–0.3 and the C ⇆ G ⇆ lamellar phase (L_α) phase transitions for concentrations about or higher than x _KC18 = 0.35. The C, G, L_α and H_α phases have been further characterized by structural parameters (characteristic d values) as a function of temperature. The phase transitions C ⇆ G, G ⇆ L_α and G ⇆ H_α correlate with sharp shifts in the d value of the first small-angle reflections. Received: 20 April 1999 Accepted: 28 July 1999     

Hydrolysis and Transglycosylation Activity of a Thermostable Recombinant β-Glycosidase from <Emphasis Type="Italic">Sulfolobus acidocaldarius</Emphasis>

We expressed a putative β-galactosidase from Sulfolobus acidocaldarius in Escherichia coli and purified the recombinant enzyme using heat treatment and Hi-Trap ion-exchange chromatography. The resultant protein gave a single 57-kDa band by SDS-PAGE and had a specific activity of 58 U/mg. The native enzyme existed as a dimer with a molecular mass of 114 kDa by gel filtration. The maximum activity of this enzyme was observed at pH 5.5 and 90 oC. The half-lives of the enzyme at 70, 80, and 90 oC were 494, 60, and 0.2 h, respectively. The hydrolytic activity with p-nitrophenyl(pNP) substrates followed the order p-nitrophenyl-β-d-fucopyranoside > pNP-β-d-glucopyranoside > pNP-β-d-galactopyranoside > pNP-β-d-mannopyranoside > pNP-β-d-xylopyranoside, but not toward aryl-α-glycosides or pNP-β-l-arabinofuranoside. Thus, the enzyme was actually a β-glycosidase. The β-glycosidase exhibited transglycosylation activity with pNP-β-d-galactopyranoside, pNP-β-d-glucopyranoside, and pNP-β-d-fucopyranoside in decreasing order of activity, in the reverse order of its hydrolytic activity. The hydrolytic activity was higher toward cellobiose than toward lactose, but the transglycosylation activity was lower with cellobiose than with lactose.     

Conjugates of polyhedral boron compounds with carbohydrates 6. Synthesis of glycoconjugates of closo-ortho-carborane with β-lactosylamine and β-d-galactopyranosylamine derivatives as galectin bi- and trivalent ligands

Five glycoconjugates were obtained from ortho-carboranylacetic acid and β-actosylamine or β-d-galactopyranosylamine derivatives with the terminal amino group in the spacer. The glycoconjugates have different lengths of the spacer (9 to 15 atoms) and contain two or three βlactosylamine residues or one, two, or three β-d-galactopyranosylamine residues.