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PubMed1989

Effect of sulfate concentration on glycosaminoglycan synthesis in explant cultures of bovine articular cartilage.

The effects of the sulfate- and FCS concentration on the rate of synthesis and the biochemical properties of glycosaminoglycans, synthesized in bovine articular cartilage in vitro, were studied. 20% FCS in the culture medium stimulated the rate of synthesis. In media without FCS, the rate of synthesis decends from day 0 on. The differences in incorporation rates of [35S]-sodium sulfate and 1,6-[3H]-glucosamine-HCl into glycosaminoglycans in serum free media containing 9 microM and 900 microM sulfate were used to discuss the inorganic sulfate concentration in cartilage. In 9 microM sulfate medium, the newly synthesized glycosaminoglycans contain higher levels of unsulfated disaccharides than the endogenous glycosaminoglycans. In each culture medium, the ratio 6-sulfated disaccharides to 4-sulfated disaccharides of the newly synthesized glycosaminoglycans becomes higher after 3 days in culture. The glycosaminoglycan synthesis is underestimated, when chondrocytes are cultured in media containing less than 200 microM sulfate.

Animals↗
PubMed1996

A highly practical synthesis of the sialyl Lewis X pentasaccharide and an investigation of binding to E-, P-, and L-selectins.

A practical synthesis of the sialyl Lewis X (sLex) pentasaccharide, NeuAc alpha 2-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc beta 1-3Gal beta OEt (1), as a potential blocker for E-selectin has been described. The glycosylation of a trisaccharide acceptor, Fuc alpha (1-3)GlcNAc beta (1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha (2-3)Gal beta SMe, did not yield the desired sLex pentasaccharide 1 at all. However, the glycosylation of a disaccharide acceptor, GlcNAc beta (1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha (2-3)Gal beta SMe, quantitatively yielded the tetrasaccharide NeuAc alpha (2-3)Gal beta (1-4)GlcNAc beta (1-3)Gal beta OEt. This tetrasaccharide is readily converted to the title compound in a high yield by fucosylation, followed by deprotection. The inhibitory activities of compound 1 toward the binding of the natural ligand (sLex) with the E-, P-, and L-selectins were stronger than those of the sLex tetrasaccharide.

Anti-Inflammatory Agents↗
PubMed2004

Matrix proteoglycans are markedly affected in advanced laryngeal squamous cell carcinoma.

Proteoglycans (PGs) are implicated in the growth and progression of malignant tumors. In this study, we examined the concentration and localization of PGs in advanced (stage IV) laryngeal squamous cell carcinoma (LSCC) and compared with human normal larynx (HNL). LSCC and HNL sections were examined immunohistochemically with a panel of antibodies, and tissues extracts were analyzed by biochemical methods including immunoblotting and high performance liquid chromatography (HPLC). The results demonstrated significant destruction of cartilage in LSCC, which was followed by marked decrease of aggrecan and link protein. In contrast to the loss of aggrecan in LSCC, accumulation of versican and decorin was observed in the tumor-associated stroma. Biochemical analyses indicated that aggrecan, versican, decorin and biglycan comprise the vast majority of total PGs in both healthy and cancerous tissue. In LSCC the absolute amounts of KS/CS/DS-containing PGs were dramatically decreased about 18-fold in comparison to HNL. This decrease is due to the loss of aggrecan. Disaccharide analysis of CS/DSPGs from LSCC showed a significant reduction of 6-sulfated Delta-disaccharides (Deltadi-6S) with a parallel increase of 4-sulfated Delta-disaccharides (Deltadi-4S) as compared to HNL. The obtained data clearly demonstrate that tumor progression is closely related to specific alteration of matrix PGs in LSCC. The altered composition of PGs in cartilage, as well as in tumor-associated stroma, is crucial for the biological behaviour of cancer cells in the diseased tissue.

Biomarkers, Tumor↗
PubMed2004

An effective synthesis of an arabinogalactan with a beta-(1-->6)-linked galactopyranose backbone and alpha-(1-->2) arabinofuranose side chains.

An octasaccharide, beta-D-Galp-(1-->6)-[alpha-L-Araf-(1-->2)]-beta-D-Galp-(1-->6)-beta-D-Galp-(1-->6)-[alpha-L-Araf-(1-->5)-alpha-L-Araf-(1-->2)]-beta-D-Galp-(1-->6)-beta-D-Galp-1-->OMP was synthesized. 4-methoxyphenyl 2,3,4-tri-O-benzoyl-beta-D-galactopyranoside (5), 2,6-di-O-acetyl-3,4-di-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (9), and 4-methoxyphenyl 2-O-acetyl-3,4-di-O-benzoyl-beta-D-galactopyranoside (11), 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (12), and 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl trichloroacetimidate (17) were used as the synthons. A concise route was used to gain the tetrasaccharide donor 19 by the use of 11, 12, 5, and 17. Meanwhile, treatment of 5 with 9 yielded beta-(1-->6)-linked disaccharide 20, and subsequent selective 6-O-deacetylation produced the disaccharide acceptor 21. Reaction of 21 with 19 gave 22, and subsequent selective 2-O-deacetylation afforded the hexasaccharide acceptor 23. Condensation of 23 with alpha-L-(1-->5)-linked arabinofuranose disaccharide 24, followed by deprotection, yielded the target octasaccharide.

Arabinose↗
PubMed2004

Synthesis of a hexasaccharide fragment of the O-deacetylated GXM of C. neoformans serotype B.

beta-D-Xylp-(1-->4)-alpha-D-Manp-(1-->3)-[beta-D-Xylp-(1-->2)]-alpha-D-Manp-(1-->3)-[beta-D-Xylp-(1-->2)]-alpha-D-Manp, the fragment of the exopolysaccharide from Cryptococcus neoformans serovar B, was synthesized as its methyl glycoside. Thus, acetylation of allyl 3-O-benzoyl-4,6-O-benzylidene-alpha-D-mannopyranoside (1) followed by debenzylidenation and selective 6-O-benzoylation afforded allyl 2-O-acetyl-3,6-di-O-benzoyl-alpha-D-mannopyranoside (4). Glycosylation of 4 with 2,3,4-tri-O-benzoyl-D-xylopyranosyl trichloroacetimidate (5) furnished the beta-(1-->4)-linked disaccharide 6. Deallylation followed by trichloroacetimidate formation gave the disaccharide donor 8, and subsequent coupling with allyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-4,6-di-O-benzoyl-alpha-D-mannopyranoside (9), produced the tetrasaccharide 10. Reiteration of deallylation and trichloroacetimidate formation from 10 yielded the tetrasaccharide donor 12. The downstream disaccharide acceptor 18 was obtained by condensation of 5 with methyl 3-O-acetyl-4,6-O-benzylidene-alpha-D-mannopyranoside, followed by debenzylidenation, benzoylation, and selective 3-O-deacetylation. Coupling of 18 with 12 afforded the hexasaccharide 19, and subsequent deprotection gave the hexasaccharide glycoside 20. Selective 2"-O-deacetylation of 19 gave the hexasaccharide acceptor 21. Condensation of 21 with glucopyranosyluronate imidate 22 did not produce the expected heptasaccharide glycoside; instead, a transacetylation product 19 was obtained. Meanwhile, there was no reaction between 21 and the bromide donor 23.

Acetamides↗
PubMed2005

An efficient and concise synthesis of a beta-(1-->6)-linked D-galactofuranosyl hexasaccharide.

A beta-(1-->6)-linked D-galactofuranosyl hexasaccharide was synthesized efficiently in a block construction manner by the well-known Schmidt glycosylation method using 6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl trichloroacetimidate (1) and allyl 2,3,5-tri-O-benzoyl-beta-D-galactofuranoside (3) as the key synthons. Coupling of 3 with 1 gave beta-(1-->6)-linked disaccharide 4. Subsequent selective deacetylation of 4 afforded the disaccharide acceptor 5, while deallylation of 4 followed by trichloroacetimidate formation produced the disaccharide donor 6. Condensation of 5 with 6 gave the tetrasaccharide 7, and subsequent deacetylation afforded the tetrasaccharide acceptor 8. Finally, coupling of 8 with 6 followed by deacylation yielded the target beta-(1-->6)-linked galactofuranose hexasaccharide 10. All of the reactions in the synthesis were carried out smoothly and in high yield.

Carbohydrate Sequence↗
PubMed2006

Synthesis of monodeoxy analogues of the trisaccharide alpha-D-Glcp-(1-->3)-alpha-D-Manp-(1-->2)-alpha-D-ManpOMe recognised by Calreticulin/Calnexin.

Six (3,4,4',6',3'' or 6'')-monodeoxy analogues of the title trisaccharide (1-6) have been prepared utilising monodeoxy monosaccharide precursors. The reducing end deoxy derivatives were synthesised by N-iodosuccinimide/silver trifluoromethanesulfonate (NIS/AgOTf)-promoted couplings of a common disaccharide thioglycoside donor 10 to suitably protected monodeoxy acceptors 9 and 12, affording trisaccharides, which after deprotection yielded target structures 1 and 2. The non-reducing end deoxy derivatives could similarly be produced by halide-assisted glycosylations of a common disaccharide acceptor 17 with monodeoxy glycosyl bromide donors (obtained from thioglycosides 18 and 20) to yield, after removal of protecting groups, target trisaccharides 3 and 4. The analogues with the deoxy function in the middle mannose residue, were obtained through orthogonal halide-assisted coupling of tetrabenzyl-glucopyranosyl bromide to monodeoxy thioglycoside acceptors to give thioglycoside disaccharides, which subsequently were used as donors in NIS/AgOTf-promoted couplings to a common 2-hydroxy-mannose acceptor 15 to afford trisaccharides; deprotection yielded the final target compounds 5 and 6.

Calnexin↗
PubMed2005

Oligosaccharide analysis using anion attachment in negative mode electrospray mass spectrometry.

Eleven different anionic species were able to form adducts with neutral oligosaccharides at low cone voltage in negative ion mode electrospray mass spectrometry. Among them, fluoride and acetate have the ability to significantly enhance the absolute abundance of [M - H](-) for neutral oliogosaccharides, which otherwise have low tendencies to deprotonate due to the lack of a highly acidic group. Evidence shows that the source of high abundances of [M - H](-) for neutral oligosaccharides arises from the decomposition of [M + F](-) and [M + Ac](-) with neutral losses of HF and HAc, respectively. The chloride adducts have the best stability among all the adduct species investigated, and chloride adducts consistently appeared in higher abundances relative to [M - H](-). In tandem mass spectrometry (ES-MS/MS) experiments, upon collision induced dissociation (CID), F(-) and Ac(-) adducts gave purely analyte-related product ions, i.e., no detection of the attaching anion and no incorporation of these anions into decomposition products. Cl(-) adducts produced both Cl(-) and analyte-related product ions. For the above three anions, CID of adduct species may be used for structural determination of neutral oligosaccharides because, in each case, structurally-informative fragment ions were produced. In the presence of F(-) and Ac(-), simultaneous detection of acidic and neutral oligosaccharides was achieved, because the problem of the presence of an acidic group that can impede the deprotonation of a neutral oligosaccharide was minimized. The ratio of Cl(-):non-Cl-containing product ions obtained in CID spectra of chloride adducts of disaccharides was used to differentiate anomeric configurations of disaccharides. Density functional theory (DFT) was employed to evaluate the optimized structures of chloride adducts of disaccharides, and it was found that chloride anions favor close contact with the hydrogen from the anomeric hydroxyl group. Multiple hydrogen bonding further stabilizes the chloride adduct.

Anions↗
PubMed2006

Effects of sulfate position on heparin octasaccharide binding to CCL2 examined by tandem mass spectrometry.

Chemokine-glycosaminoglycan (GAG) interactions have been shown to be essential for in vivo chemokine signaling, which functions in such diverse processes as inflammation, development, and cancer metastasis. Despite the importance of these interactions, the saccharide sequence dependency of chemokine-GAG interactions is poorly understood. In a recent study, FT-ICR mass spectrometry was used to show that the chemokine CCL2 (monocyte chemoattractant protein 1) binds only to the 11- and 12-sulfated components of a heparin octasaccharide library. Although the exact structure of the fully sulfated, 12-sulfated octasaccharide is known, the 11-sulfated species could have a number of sulfated disaccharide sequences. In the current study, the composition of the 11-sulfated heparin octasaccharides, as well as the composition of CCL2 affinity purified 11-sulfated heparin octasaccharides, were examined by tandem MS. Of the three possible singly desulfated disaccharides, one species, III-S, is enriched by CCL2 affinity purification, indicating that the 11-sulfated heparin octasaccharides containing this disaccharide are preferentially bound to CCL2. These data suggest that 2-O and N sulfation of heparin may be of greater importance to CCL2-heparin binding than 6-O sulfation.

Binding Sites↗
PubMed2005

Decorin from different bovine tissues: study of glycosaminoglycan chain by PAGEFS.

The sulphation pattern of glycosaminoglycan (GAG) plays a critical role in biological functions of proteoglycans. In this study, we showed that decorins from different bovine tissues present specific sulphation pattern coupled with peculiar biological activity. In order to elucidate chemical structure of decorin glycosaminoglycan chains, we improved an electrophoretic method to analyse fluorescent disaccharides from dermatan/chondroitin sulphate GAG chains. The disaccharide separation is based on minigels, and this technique was able to define the polysaccharide chain composition in terms of sulphated and not sulphated disaccharides. This approach allowed not only the measurement of few picomoles of material, but it also permits a rapid qualitative analysis of the GAG chains. Data obtained by PAGEFS indicate that the sulphation pattern of GAG is tissue specific and this finding may explain the different binding properties to von Willebrand factor of decorins.

Animals↗
PubMed1993

Adsorption to ice of fish antifreeze glycopeptides 7 and 8.

Experimental results show that fish antifreeze glycopeptides (AFGPs) 8 and 7 (with 4 and 5 repeats respectively of the Ala-Ala-Thr backbone sequence) bond onto ice prism planes aligned along a-axes, and inhibit crystal growth on prism planes and on surfaces close to that orientation. The 9.31-A repeat spacing of the AFGP in the polyproline II helix configuration, deduced from NMR studies, matches twice the repeat spacing of ice in the deduced alignment direction, 9.038 A, within 3%. A specific binding model is proposed for the AFGP and for the alpha-helical antifreeze peptide of winter flounder. For AFGP 7-8, two hydroxyl groups of each disaccharide (one disaccharide is attached to each threonine) reside within the ice surface, so that they are shared between the ice crystal and the disaccharide. This provides 24 hydrogen bonds between AFGP 8 and the ice and 30 for AFGP 7, explaining why the chemical adsorption is virtually irreversible and the crystal growth can be stopped virtually completely. The same scheme of sharing polar groups with the ice works well with the alpha-helical antifreeze of winter flounder, for which an amide as well as several hydroxyls are shared. The sharing of polar groups with the ice crystal, rather than hydrogen-bonding to the ice surface, may be a general requirement for adsoprtion-inhibition of freezing.

Adsorption↗
PubMed2000

The efficient enzymatic synthesis of N-acetyllactosamine in an organic co-solvent.

In the presence of beta-galactosidase from Bifidobacterium bifidum, N-acetyllactosamine was synthesized in significantly enhanced yield compared with earlier routes. Different proportions of the (1-->4)- and (1-->6)-linked forms were obtained depending on the choice of enzyme and reaction conditions, viz. the nature of added organic co-solvent (20-80% of 2-ethoxy ethyl ether, trimethyl phosphate, or acetone). The beta-(1-->4)-linked disaccharide was the major product and the beta-(1-->6)-linked disaccharide was the minor product. With beta-galactosidases from P. multicolor, A. oryzae, B. longum the beta-(1-->6) linkage was exclusively synthesized. Procedures for optimising the yield of N-acetyllactosamine are discussed. An immobilized enzyme on a nylon powder column was used for the efficient recycling of enzyme and synthesizing the disaccharide.

Amino Sugars↗
PubMed2000

Synthesis of neoglycoproteins containing D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko) ligands corresponding to core units from Burkholderia and Acinetobacter lipopolysaccharide.

Glycal esters of Kdo derivatives were converted into 2,3-anhydro intermediates, which were transformed into D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko), as well as 3-O- and 4-O-p-nitrobenzoyl-Ko derivatives. The exo-allyl orthoester derivative, methyl [5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-2,3-O-[(1-exo-allyloxy)-ethylidene]-D-glycero-beta-D-talo-oct-2-ulopyranos]onate, prepared from the 4-O-pNBz-protected Ko derivative, was elaborated into the alpha-Ko allyl ketoside, the reducing disaccharide alpha-Kdop-(2-->4)-Ko and the disaccharide alpha-Kdop-(2-->4)-Kop-(2-->OAll). Conversely, methyl[4,5,7,8-tetra-O-acetyl-3-O-(4-nitrobenzoyl)-alpha-D-glycero-D-talo-2-octulopyranosyl bromide]onate [Carbohydr. Res., 244 (1993) 69-84], was coupled with a Kdo acceptor to give the disaccharide alpha-Kop-(2-->4)-Kdop-(2-->OAll) after orthoester rearrangement and deprotection. The allyl glycosides were treated with cysteamine and converted into neoglycoproteins. The ligands correspond to inner core units from Acinetobacter haemolyticus and Burkholderia cepacia lipopolysaccharides.

Acinetobacter↗
PubMed1981

Purification of heparinase and heparitinase by affinity chromatography on glycosaminoglycan-bound AH-Sepharose 4B.

Heparinase and heparitinase were separated from an extract of Flavobacterium heparinum, induced with heparin by using column chromatography on hydroxylapatite. As the heparinase preparation contained chondroitinases B and C, chondroitinase B was removed by rechromatography on a hydroxylapatite column. Chondroitinase C was then eliminated by column chromatography on O-phosphono("phospho")-cellulose. The heparinase preparation thus obtained was free from sulfoamidase for 2-deoxy-2-sulfoamino-D-glucose (GlcN-2S), sulfatase for 2-amino-2-deoxy-6-O-sulfo-D-glucose (GlcN-6S), as well as delta 4,5glycosiduronase for the unsaturated disaccharides obtained from heparin. The remaining sulfatase for 4-deoxy-alpha-L-threo-hex-4-enopyranosyluronic acid 2-sulfate (delta UA-2S) in the heparinase preparation was removed by affinity chromatography with dermatan sulfate-bound AH-Sepharose 4B coated with dermatan sulfate. The heparitinase preparation separated by column chromatography on hydroxylapatite was purified by affinity chromatography with heparin-bound AH-Sepharose 4B coated with heparin. Sulfatase for 2-amino-2-deoxy-6-O-sulfo-D-glucose (GlcN-6S) and delta 4,5glycosiduronase for the unsaturated disaccharides obtained from heparin were removed by this chromatography. Sulfatase for 4-deoxy-alpha-L-threo-hex-4-enopyranosyluronic acid 2-sulfate (delta UA-2S) remaining in the heparitinase preparation was finally removed by column chromatography on hydroxylapatite. The recoveries of the purified preparations of heparinase and heparitinase were estimated to be 39 and 50%, respectively, from the crude enzyme fractions obtained by the first column chromatography on hydroxylapatite. The purified heparinase and heparitinase were free from all enzymes that could degrade the sulfated unsaturated disaccharides produced from heparin with heparinase.

Chromatography, Affinity↗
PubMed1986

Glycoproteins of human teratocarcinoma cells (PA1) carry both anomers of O-glycosyl-linked D-galactopyranosyl-(1----3)-2-acetamido- 2-deoxy-alpha-D-galactopyranosyl group.

Two disaccharide alcohols, alpha-D-Galp(1----3)-GalNAcol and beta-D-Galp-(1----3)-GalNAcol, together with a GalNAcol-containing tetra- or penta-saccharide alcohol, were released from human embryonal carcinoma cells of line PA1 by reductive beta-elimination. The disaccharides were identified by exoglycosidase digestions and by periodate oxidation. The results were confirmed by affinity chromatography of the disaccharide alcohols on immobilized Bandeirea simplicifolia lectin and by chromatography of the parent glycopeptides on immobilized peanut lectin.

Carbohydrate Conformation↗
PubMed2002

Synthesis of alpha-Manp-(1-->2)-alpha-Manp-(1-->3)-alpha-Manp-(1-->3)-Manp, the tetrasaccharide repeating unit of Escherichia coli O9a, and alpha-Manp-(1-->2)-alpha-Manp-(1-->2)-alpha-Manp-(1-->3)-alpha-Manp-(1-->3)-Manp, the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3.

The tetrasaccharide repeating unit of Escherichia coli O9a, alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-D-Manp, and the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3, alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-D-Manp, were synthesized as their methyl glycosides. Thus, selective 3-O-allylation of p-methoxyphenyl alpha-D-mannopyranoside via a dibutyltin intermediate gave p-methoxyphenyl 3-O-allyl-alpha-D-mannopyranoside (2) in good yield. Benzoylation (-->3), then removal of 1-O-methoxyphenyl (right arrow4), and subsequent trichloroacetimidation afforded the 3-O-allyl-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (5). Condensation of 5 with methyl 4,6-O-benzylidene-alpha-D-mannopyranoside (6) selectively afforded the (1-->3)-linked disaccharide 7. Benzoylation of 7, debenzylidenation, benzoylation, and deallylation gave methyl 2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (11) as the disaccharide acceptor. Coupling of 11 with (1-->2)-linked mannose disaccharide donor 17 or trisaccharide donor 21, followed by deacylation, furnished the target tetrasaccharide and pentasaccharide, respectively.

Carbohydrate Sequence↗
PubMed2002

Preparation of orthogonally protected chitosan oligosaccharides: observation of an anomalous remote substituent effect.

Orthogonally protected chitosan tetrasaccharides were synthesized in a convergent fashion by trichloroacetimidate activation. The anomeric substituent at the reducing end of the disaccharide acceptor has a remarkably strong influence on glycosidic coupling; a thiophenyl-substituted disaccharide was observed to be an unusually poor glycosyl acceptor in comparison with the corresponding allyloxy-substituted disaccharide.

Chitin↗
PubMed2003

Depicting the MM3 potential energy surfaces of trisaccharides by single contour maps: application to beta-cellotriose and alpha-maltotriose.

The adiabatic potential energy surfaces (PES) of two trisaccharides (beta-cellotriose and alpha-maltotriose) were obtained using the MM3 force field. Each PES can be described by a single 3D contour map for which the energy is plotted against the two psi glycosidic angles. Given the usually small variations of the phi glycosidic torsional angle in the low-energy regions of disaccharide maps (at least with MM3), it is valid to leave both phi glycosidic angles to relax in the process of building the conformational map of trisaccharides. The surfaces are those expected from the map of disaccharides containing the same linkages and monosaccharide units (i.e., beta-cellobiose and alpha-maltose), with second-order factors altering the 'symmetry' of both linkages. A large low-energy region appears for beta-cellotriose, comprising four minima in close proximity, with barriers between them below 0.6 kcal/mol. On the other hand, for alpha-maltotriose a main global minimum is observed, with several surrounding local minima. The surfaces obtained agree with single-crystal X-ray data on these trisaccharides and derivatives. A reduction of the linkage flexibilities is observed when passing from the disaccharides to the trisaccharides. Furthermore, the linkage closer to the reducing end appears to be less flexible than the linkage closer to the non-reducing end.

Carbohydrate Conformation↗