[Effect of aluminium hydroxide on innate immunity and immunogenicity of bacterial and synthetic antigens of Streptococcus pneumoniae].

AIM: Study the effect of aluminium hydroxide on molecular-cell mechanisms of innate immunity activation and its adjuvant effect on immunogenicity of natural bacterial and synthetic pneumococci antigens. MATERIALS AND METHODS: Surface markers of dendritic cells (DC), mononuclear leukocytes (ML) and cytokine levels were determined by flow cytometry; IgG titers--by EIA. Protective activity was evaluated in experiments with active protection of mice from infection with virulent pneumococci strains. RESULTS: Aluminium hydroxide increased the ML content of mice spleen expressing TLR2 and TLR4. Its addition into the culture of immature DC induced the appearance of a population of cells with mature DC markers--CD83, CD80, CD86, however, the level of undifferentiated cells (CD34) and cells with adhesion molecules (CD11c, CD38) did not change. DC produced IL-1ß, IL-5, IL-10, IFNγ into the cultivation medium. An increase of cytokine production took place 2 hours after the administration into mice and was retained for the observation period (24 hours). Th1 (IFNγ, TNFα) and Th2 (IL-5, IL-10, GM-CSF) cytokine production gave evidence on immune response polarization by Th1/Th2, type. After 2 administrations of aluminium hydroxide into mice the number of ML with CD19+, CD5+, NK1.1+, CD25+, MHCII+ markers increased during decrease of CD3+, CD4+ and CD8+ T-lymphocytes. Adaptive immunity activation was characterized by high IgG titers to pneumococci capsule polysaccharide and protection of 90 - 100% of the mice against infection with lethal doses of S. pneumoniae strains, was detected during 2-fold immunization of mice with conjugates of synthetic pneumococci oligosaccharides with BSA,sorbed onto aluminium hydroxide, whereas natural bacterial antigens provided 90 - 100% survival of animals during immunization without the adjuvant. CONCLUSION: Data are provided on the effect of aluminium hydroxide on key effectors of innate immunity: DC, ML, TLRs and cytokine production. A reasonable administration of this adjuvant was shown to be in association with conjugates of pneumococci synthetic oligosaccharides with a carrier protein.

[Conjugates of cyclooligosaccharide scaffolds and carbohydrate ligands: methods of synthesis and interaction with lectins].

Main approaches to the preparation of mono- and oligodentate glycoconjugates based on cyclodextrin and cyclooligo-ß-(1 -> 6)-D-glucosamine scaffolds are surveyed in the review. The data on the biological activity of the glycoconjugates by the example of their interaction with lectins are discussed.

[Strain differences of intra-species immunogenic activity of Streptococcus pneumoniae antigen components].

AIM: Study intra-species immunogenic activity of antigenic protein-polysaccharide components of S. pneumoniae. MATERIALS AND METHODS: Antigenic components of serotype 3, 6A, 6B, 14, 10A, 18A, 19A, 19F, 23F and unencapsulated S. pneumoniae strains were obtained by water extraction method. Synthetic hexasaccharide--corresponding to the structure of S. pneumoniae serotype 14 capsule polysaccharide repeated unit chain fragment was used as a reference preparation. Molecular mass of antigenic components was determined in SDS-electrophoresis. Antibody titers in blood sera of immunized mice were evaluated by solid-phase EIA method. Protective activity of preparations was studied in mice after 2 immunizations with consequent infection by virulent S. pneumoniae serotype 3 and 6B strains. RESULTS: Preparations from serotype 6A, 6B, 14, 19A, 19F, 23F strains in reaction with anti-microbial sera were characterized by cross serologic activity (IgG titers of 1200 - 12 800). The lowest serologic activity was detected in S. pneumoniae serotype 3 and unencapsulated strain preparations. Conjugate of synthetic hexasaccharide and bovine serum albumin interacted only with homologous antimicrobial sera up to titers of 600 +/- 89.4 and did not react with sera against serotypes 19A and 19E Cross serologic activity of preparations is probably determined by the presence of protein fractions that were detected in SDS-electrophoresis. This is confirmed by high intra-species cross protective activity of preparations from serotype 6B and 10 A strains that protect 90 - 100% of mice from infection by heterologous S. pneumoniae strains. CONCLUSION: Use of strains with cross antigenic and protective activity for production of immunogenic protein-containing fractions with the aim of enchanting and broadening specter of protective activity of vaccine preparations that are constructed based on capsule polysaccharides of S. pneumoniae is appropriate.

[Immunogenic activity of a conjugate of synthetic hexasaccharide related to a streptococcus pneumoniae serotype 14 capsule polysaccharide chain fragment].

AIM: Study antigenic and immunogenic activity of a conjugate of synthetic hexasaccharide related to a S. pneumoniae serotype 14 capsule polysaccharide chain fragment with bovine serum albumin (BSA). MATERIALS AND METHODS: Synthetic glucoconjugate based on BSA protein carrier and hexasaccharide ligand reflecting capsule polysaccharide chain fragment was obtained by using squarate method. Natural polysaccharide-protein complex from S. pneumoniae serotype 14 strain was obtained from cultural fluid supernatant by acetone precipitation. IgG titer against hexasaccharide/capsule polysaccharide was determined in antimicrobial sera and sera of mice immunized with glucoconjugate by EIA method. RESULTS: Immunogenic activity ofglucoconjugate based on BSA protein carriers and synthetic hexasaccharide reflecting S. pneumoniae serotype 14 capsule protein chain fragment was established. After 2 immunizations antibodies against hexasaccharide ligand and BSA were determined in blood sera of mice. Antibody titers against hexasaccharide exceeded the level in intact mice by 4.2 times. BSA in the conjugate did not have effect on production of antibodies against hexasaccharide. CONCLUSION: The developed experimental test-system based on synthetic glucoconjugate is useful for evaluation of level of antibodies against S. pneumoniae serotype 14 in infected and, probably, carriers of bacteria.

[Synthesis of oligosaccharide fragments of mannan from Candida albicans cell wall and their BSA conjugates].

3-Aminopropyl glycosides of alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyra-nosyl-(1-->2)-alpha-D-mannopyranose, alpha-D-mannopyranosyl-(1-->3)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(l -- 2)-alpha-D-mannopyranose, and alpha-D-mannopyranosyl-(1-->2)-[alpha-D-mannopyranosyl-(1-->3)]-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose were efficiently synthesized starting from ethyl 2-O-acetyl(benzoyl)-3,4,6-tri-O-benzyl-l-thio-alpha-D-mannopyranoside, ethyl 4,6-di-O-benzyl-2-O-benzoyl-1-thio-alpha-D-mannopyranoside, ethyl 4,6-di-O-benzyl-2,3-di-O-benzoyl-l-thio-alpha-D-mannopyranoside, and 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl bromide. The oligosaccharide chains synthesized correspond to the three structural types of side chains of mannan from Candida albicans cell wall. A conjugate of the third pentasaccharide with bovine serum albumin was prepared using the squarate method.

[The study of the reaction of terminated oligomerization in the synthesis of oligo-(beta1-6)-glucosamines].

The applicability of terminated oligomerization to the synthesis of oligo-(beta1-6)-glycosamines, fragments of the intercellular polysaccharide adhesin of staphylococci, was studied. The reactions of terminated oligomerization were carried out with mono-, di-, and trisaccharide monomers and N-protected aminopropanol; and spacered mono- and disaccharides as terminating molecules were also attempted. The primary formation of cyclic products of monomer intramolecular glycosylation was observed in almost all the reactions. Only the experiments with the monomer based on the disaccharide bromide under the conditions of the Helferich reaction led to reduced yields (30%) of the cyclic products. However, even in this case, the desired terminated oligosaccharides were generated in approximately 10% yield and mainly were the products of single glycosylation of the terminator by the monomer. These experiments allow the conclusion that, under the examined conditions, the reaction of terminated oligomerization could not result in the synthesis of oligoglucosamines with a high molecular mass.

[Synthesis of aminoethylglycosides with oligosaccharide GM1 and asialo-GM1 ganglioside chains]. / Sintez aminoétilglikozidov oligosakharidnykh tsepei gangliozidov GM1 i asialo-GM1.

4'-O-Glycosylation of 2-azidoethyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O- benzyl-6-O-benzoyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside with a disaccharide donor, 4-trichloroacetamidophenyl 4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl)-1-thio-2-trichloroacetamido-beta-D-galactopyranoside, in dichloromethane in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid resulted in a tetrasaccharide, 2-azidoethyl (2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->3)- (4,6-di-O-acetyl-2-deoxy-2-trichloroacetamido-beta-D-galactopyranosyl)- (1-->4)-(2,3-di-O-benzyl-6-O-benzoyl-beta-D-galactopyranosyl)- (1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside, in 69% yield. The complete removal of O-protecting groups in the tetrasaccharide, the replacement of N-trichloroacetyl by N-acetyl group, and the reduction of the aglycone azide group to amine led to the target aminoethyl glycoside of beta-D-Gal- (1-->3)-beta-D-GalNAc-(1-->4)-beta-D-Gal-(1-->4)-beta-D-Glc-OCH2CH2NH2 containing the oligosaccharide chain of asialo-GM1 ganglioside in 72% overall yield. Selective 3'-O-glycosylation of 2-azidoethyl 2,3,6-tri-O- benzyl-4-O-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside with thioglycoside methyl (ethyl 5-acetamido-4,7,8,9-tetra-O- acetyl-3,5-dideoxy-2-thio-D-glycero-alpha-D-galacto-2-nonulopyranosyl)oate in acetonitrile in the presence of N-iodosuccinimide and trifluoroacetic acid afforded 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl- 3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosyl)oate in acetonitrile in the presence of N-iodosuccinimide and tri-fluoracetic acid afforded 2-azidoethyl[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl- 3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosyl) (2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D- glucopyranoside, the selectively protected derivative of the oligosaccharide chain of GM3 ganglioside, in 79% yield. Its 4'-O-glycosylation with a disaccharide glycosyl donor, (4-trichloroacetophenyl-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O- acetyl-beta-D-galactopyranosyl) 1-thio-2-trichloroacetamido-beta-D-galactopyranoside in dichloromethane in the presence of N-iodosuccinimide and trifluoroacetic acid gave 2-azidoethyl (2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)- (1-->3)-(4,6-di-O-acetyl-2-deoxy-2-trichloroacetamido-beta-D- galactopyranosyl)-(1-->4)-[[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D- galacto-2-nonulopyranosyl)onate]-(2-->3)]-(2,6-di-O-benzyl-beta-D- galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside in 85% yield. The resulting pentasaccharide was O-deprotected, its N-trichloroacetyl group was replaced by N-acetyl group, and the aglycone azide group was reduced to afford in 85% overall yield aminoethyl glycoside of beta-D-Gal-(1-->3)-beta-D-GalNAc-(1-->4)-[alpha-D-Neu5Ac-(2-->3)]- beta-D-Gal-(1-->4)-beta-D-Glc-OCH2CH2NH2 containing the oligosaccharide chain of GM1 ganglioside. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 1; see also http://www.maik.ru.

[Synthesis of aminoethyl glycosides of the carbohydrate chains of glycolipids Gb3, Gb4 i Gb5]. / Sintez aminoétilglikozidov oligosakharidnykh tsepei glikolipidov Gb3, Gb4 i Gb5.

4-O-Glycosylation of 2-azidoethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl)-beta- D-glucopyranoside with ethyl 2,3,4,6-tetra-O-benzyl- and ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-alpha-D-galactopyranoside in the presence of methyl trifluoromethanesulfonate led to trisaccharide 2-azidoethyl (2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1-->4)- (2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)2,3,6-tri-O- benzoyl-beta-D-glucopyranoside and its 3"-O-acetylated analogue, 2-azidoethyl (3-O-acetyl-2,4,6-tri-O-benzyl- alpha-D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzoyl-beta-D- galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside, in yields of 85 and 83%, respectively. Deacetylation of the latter compound and subsequent glycosylation with 4-trichloroacetamidophenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-beta-D- galactopyranoside and 4-trichloroacetamidophenyl 4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O- acetyl-beta-D-galactopyranosyl)-1-thio-2-trichloroacetamido-beta-D- galactopyranoside in dichloromethane in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid resulted in the corresponding selectively protected derivatives of tetrasaccharide GalNAc(beta 1-->3)Gal(alpha 1-->4)Gal(beta 1-->4)Glc beta-OCH2CH2N3 and pentasaccharide Gal(beta 1-->3)GalNAc(beta 1-->3)Gal(alpha 1-->4)Gal(beta 1-->4)Glc beta-OCH2CH2N3 in 88 and 73% yields, respectively. Removal of O-protecting groups, substitution of acetyl group for N-trichloroacetyl group, and reduction of the aglycone azide group resulted in the target 2-aminoethyl globo-tri-, -tetra-, and -pentasaccharide, respectively.

[Synthesis of alpha- and beta-glycosyl donors with a disaccharide beta-D-Gal-(1-->3)-D-GalNAc backbone]. / Tioglikozidnye alpha- i beta-glikozildonory na osnove disakharida beta-D-Gal-(1-->3)-D-GalNAc.

The synthesis of thioglycosyl donors with a disaccharide beta-D-Gal-(1-->3)-D-GalNAc backbone was studied using the glycosylation of a series of suitably protected 3-monohydroxy- and 3,4-dihydroxyderivatives of phenyl 2-azido-2-deoxy-1-thio-alpha- and 1-thio-beta-D-galactopyranosides by galactosyl bromide, fluoride, and trichloroacetimidate. In the reaction with the monohydroxylated glycosyl acceptor, the process of intermolecular transfer of thiophenyl group from the glycosyl acceptor onto the cation formed from the molecule of glycosyl donor dominated. When glycosylating 3,4-diol under the same conditions, the product of the thiophenyl group transfer dominated or the undesired (1-->4), rather than (1-->3)-linked, disaccharide product formed. The aglycone transfer was excluded when 4-nitrophenylthio group was substituted for phenylthio group in the galactosyl acceptor molecule. This led to the target disaccharide, 4-nitrophenyl 2-azido-4,5-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl)-1-thio-beta-D-galactopyranoside, in 57% yield. This disaccharide product bears nonparticipating azide group in position 2 of galactosamine and can hence be used to form alpha-glycoside bond. 2-Azide group and the aglycone nitro group were simultaneously reduced in this product and then trichloroacetylated, which led to the beta-glycosyl donor, 4-trichloroacetamidophenyl 4,6-O-diacetyl-2-deoxy-3-O-(2,3,4,6-tetra- O-acetyl-beta-D-galactopyranosyl)-1-thio-2-trichloroacetamido-beta-D- galactopyranoside, in 62% yield. The resulting glycosyl donor was used in the synthesis of tetrasaccharide asialo-GM1.

[Selectin receptors. 5. Monoclonal antibodies to the synthetic antigens SiaLe(a) and SiaLe(x)]. / Retseptory selektinov. 5. Monoklonal'nye antitela k sinteticheskim antigenam SiaLea i SiaLex.

Five IgM class monoclonal antibodies (MAb) to the SiaLea tetrasaccharide, which is known as a serologic tumor marker CA 19.9, and three MAbs (one of IgG3 and two of IgM class) to the SiaLex tetrasaccharide (differentiation antigen CD15s) were obtained against totally synthetic immunogens. The epitope specificity of the antibodies was determined using a wide range of oligosaccharides and their polyacrylamide conjugates. MAb 4E10 against SiaLea and MAb 4G5 to SiaLex were highly specific to the antigen predefined by immunization: they did not cross-react either with structurally and conformationally related oligosaccharides or with their disaccharide fragments. Two MAbs to SiaLea (D7 and E5B1) showed a weak binding to SiaLex. MAb CC1 recognized SiaLea and SiaLex almost equally, and MAb 5H9 to SiaLea cross-reacted with the non-sialylated form, the Lea trisaccharide. Two MAbs against SiaLex A3 and B11 bound to all carbohydrate structures containing the core disaccharide Gal beta 1-3(4)GlcNAc.

[Synthesis and study of NMR spectra and conformations of branched oligosaccharides. 2,3-di-O-glycosylated methyl-alpha-L-rhamnopyranosides with one or two 2-acetamido-2-deoxy-beta-D-glucopyranosyl residues]. / Sintez i issledovanie spektrov IaMR i konformatsii razvetvlennykh oligosakharidov. 2,3-Di-O-glikozilirovannye metil-alpha-L-ramnopiranozidy s odnim ili dvumia 2-atsetamido-2-dezoksi-beta-D-gliukopiranozil'nymi ostatkami.

A series of methyl 2,3-di-O-glycosyl-alpha-L-rhamnopyranosides with 2-acetamido-2-deoxy-beta-D-glucopyranosyl substituents have been synthesized and the deviations from additivity (delta delta) in their 13C-NMR spectra determined. It is shown that the delta delta values for the trisaccharides with the GlcNAc substituent at O-2 of the diglycosylated Rha may markedly differ from the delta delta values in the spectra of the respective trisaccharides with the Glc substituent. These deviations are probably associated with the intramolecular spatial interactions with participation of the NHAc-group.

[Selectin receptors. 1. Synthesis of SiaLe(a) and SiaLe(x) tetrasaccharides and their polymeric conjugates]. / Retseptory selektinov. 1. Sintez tetrasakharidov SiaLe(a) i SiaLe(x) i ikh polimernykh kon''iugatov.

Spacer-armed tetrasaccharide Neu5Ac alpha 2-3Gal beta 1-3(Fuc alpha 1- 4)GlcNAc-sp (SiaLe(a), sp = OCH2CH2CH2NH2) was synthesized from 6-BnGlcNAc-sp with 6-BnAc3GalSEt, Bn3FucSEt, and Ac4Neu5AcSEt methyl ester as glycosyl donors. The final glycosylation of the trisaccharide bearing unprotected 2-, 3-, and 4-hydroxyls of galactose moiety was promoted with NIS-TfOH in MeCN, yield of alpha-sialoside being 48% (29% as the NGlcNAc-SEt derivative). A mixture of beta-connected (2-3) and (2-4) lactones was obtained as a side product (30%). Tetrasaccharide Neu5Ac alpha 2-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc-sp (SiaLe(x)) was synthesized by a similar way starting from 6-Bn-3-MeOBnGlcNAc-sp; yield of alpha-sialylation was 74%, neither N-SEt nor beta-connected lactones were isolated. Condensation of the spacered tetrasaccharides with poly(4-nitrophenylacrylate) gave N-substituted polyacrylamide-type polymers. Biotinylated probes and polymers modified with phosphatidylethanolamine (strong immunogens) were also obtained. The unsubstituted and labelled polymeric derivatives were used for studying selectins and other lectins, as well as production and epitope characterization of monoclonal antibodies against sialooligosaccharides.

[Trityl-cyanoethylidene condensation of azidosaccharide derivatives as a route to hexosaminoglycans. Synthesis of the O-antigenic polysaccharide of Pseudomonas aeruginosa X (Meitert)]. / Tritil-tsianoétilidenovaia kondensatsiia proizvodnykh azidosakharov kak put' k geksozaminoglikanam. Sintez O-antigennogo polisakharida Pseudomonas aeruginosa X (Meitert).

Derivatives of azidosugars were shown to be stable under conditions of trityl-cyanoethylidene condensation. Tritylated 1,2-O-(1-cyano)ethylidene derivative of 2-azido-2-deoxy-beta-D-mannopyranosyl-(1----4)-L-rhamnopyranose was used as a starting material for the synthesis of [----3)-beta-D-ManNAc-(1----4)-alpha-L-Rha-(1----]n, the O-specific polysaccharide of Pseudomonas aeruginosa X (Meitert).

[Antibodies to the rhamnose determinants of the polysaccharide of streptococci group A in the sera of rheumatism patients and donors]. / Antitela k ramnoznym determinantam polisakharida streptokokkov gruppy A v syvorotkakh bol'nykh revmatizmom i donorov.

In the sera of patients with recurrent rheumocarditis, and especially in cases of primary rheumatism, the level of antibodies to group A streptococcal polysaccharide (A-PS) has been found, according to the results of the enzyme immunoassay, to be considerably higher than in the sera of healthy donors. The level of antibodies to rhamnose determinants (RD) of A-PS has been determined by the inhibition of the immunoenzyme reaction with A-PS under the influence of a variant of group A streptococcus and rhamnose disaccharides with the bonds alpha 1-2 and alpha 1-3. In patients with recurrent rheumocarditis the level of antibodies to A-PS has been shown to be considerably higher than in healthy donors having these antibodies. In acute primary rheumatism a high level of antibodies to A-PS has been detected only in a few cases, and at the same time the prevalence of antibodies to the specific RD of A-PS, bound with beta-N-acetylglucosamine, is observed. In the sera of patients with recurrent rheumocarditis and donors having a high content of antibodies to the rhamnose site of A-PS antibodies, seemingly active against at least two RD, have been detected. In acute primary rheumatism an insignificant amount of antibodies to the rhamnose site of A-PS may probably cause the autoimmune process accompanying rheumatism. This suggestion is substantiated by the previously established capacity of these antibodies for inducing the suppression of cytotoxic cell reactions to microbial antigens.

[Immune response to a synthetic polysaccharide and protein conjugate]. / Immunnyi otvet k kon"iugatu sinteticheskogo polisakharida s belkom.

Synthetic polysaccharide (S-PS) containing aglycone-spacer with a free amino group was really alpha 1,6-mannan with Cn approximately 10. S-PS was transformed into isothiocyanate derivative by treating it with thiophosgene and engaged into reaction with amino group of bovine serum albumin (BSA) lysine residues. Rabbits were immunized with S-PS-BSA conjugate and antibodies to S-PS titres were estimated by means of ELISA. S-PS-BSA conjugate was proved to provoke specific anti-polysaccharide antibodies formation in rabbits.

[Synthesis of the polysaccharide common antigen of Pseudomonas aeruginosa and its L-analog in the form of 6-aminohexyl glycosides]. / Sintez polisakharidnogo obshchego antigena Pseudomonas aeruginosa i ego L-analoga v forme (6-aminogeksil)glikozidov.

A synthesis of trisaccharide monomers built of D- or L-rhamnose residues is described. Their polycondensation in the presence of a 6-aminohexyl rhamnoside derivative afforded 6-aminohexyl glycosides of the natural common polysaccharide antigen of Pseudomonas aeruginosa and its L-analogue, respectively.

[Synthesis of 6-aminohexylglycosides of a polysaccharide from Streptococcus group A and its fragments]. / Sintez 6-aminogeksilglikozidov polisakharida streptokokkov gruppy A-variant i ego fragmentov.

Polycondensation of 4-O-benzoyl-1,2-O-(1-cyanoethylidene)-3-O-(3,4-di-O-benzoyl-2-O-tr ityl-alpha-L- rhamnopyranosyl)-beta-L-rhamnopyranose in the presence of 6-phthalimidohexyl-3,4-di-O-benzoyl-2-O-trityl-alpha-L- rhamnopyranoside affords, after deprotection, the polysaccharide built up of the repeating dissaccharide units----2) Rha (alpha 1----3) Rha (alpha 1----and containing 6-aminohexyl residue at the reducing end. This polysaccharide possesses the structure of the group A-variant streptococcal polysaccharide. Synthesis of 6-aminohexyl glycosides of 2- and 3-O-alpha-L-rhamnopyranosyl-alpha-L-rhamnopyranoses, which corresponds to the repeating units of the above polysaccharide, is described.

[Synthesis of a repeating unit and the dimer of the repeating unit of the major chain of Shigella flexneri O-antigen polysaccharide]. / Sintez povtoriaiushchegosia zvena i dimera povtoriaiushchegosia zvena osnovnoi tsepi O-antigennykh polisakharidov Shigella flexneri.

Methyl glycoside of the tetrasaccharide GlcNAc(beta 1-2)Rha(alpha 1-2)Rha(alpha 1-3)Rha, which represents a repeating unit of the basic chain of Shigella flexneri O-antigenic polysaccharides, was synthesized using acylated monosaccharide synthons. A dimer of the repeating unit, octasaccharide [GlcNAc(beta 1-2)Rha(alpha 1-2) Rha(alpha 1-3)Rha(alpha 1-3)]2-OMe was obtained by TrClO4-catalyzed condensation of two tetrasaccharide blocks.