Chemical synthesis of 6-deoxy-D-talose containing a tetrasaccharide repeating unit of the O-specific polysaccharide from G3422 in the form of its 2-aminoethyl glycoside.

Chemical synthesis of the tetrasaccharide repeating unit of the O-specific polysaccharide from G3422 is reported. The synthesis of the target tetrasaccharide is achieved through a convergent [2 + 2]-block strategy. The conjugation ready target oligosaccharide is attractive for further glycoconjugate formation with a suitable aglycon.

Synthesis of the Hexasaccharide Related to the Exopolysaccharide from VG1 through Regioselective Glycosylation.

Chemical synthesis of the hexasaccharide repeating unit associated with the exopolysaccharide of VG1 is reported. The total synthesis is accomplished through a convergent [2 + 2 + 2] strategy using rationally protected monosaccharide derivatives. Chemoselective activation of the glycosyl donors and regioselective nucleophilicity of the acceptors were successfully employed throughout the chemical synthesis.

Chemical synthesis of the pentasaccharide repeating unit of the O-antigen from Escherichia coli strain SDLZB008 in the form of its 2-aminoethyl glycoside.

Chemical synthesis of the pentasaccharide repeating unit of the O-antigen from E. coli strain SDLZB008 is accomplished through a linear strategy using rationally protected monosaccharide derivatives ensuring desired stereochemical outcome up on glycosylations. 2-Aminoethyl glycoside is incorporated at the reducing end of the target pentasaccharide.

Chemical synthesis of β-D-ManNAc containing pentasaccharide repeating unit of the exopolysaccharide from Lactobacillus rhamnosus BIM B-1039 in the form of its p-methoxyphenyl glycoside.

Total synthesis of the pentasaccharide repeating unit of the exopolysaccharide from Lactobacillus rhamnosus BIM B-1039 is accomplished by bis-glycosylation on a suitably protected trisaccharide di-ol. The stereochemically challenging β-D-ManNAc residue was introduced through a glucose derivative to ensure β-selectivity followed by inversion of the 2-OH position with azido group to form the desired mannosamine moiety. The use of the p-methoxyphenyl glycoside at the reducing end was triggered by the fact that its oxidative cleavage followed by the formation of the trichloroacetimidate derivative will open up the scope for further conjugation of suitable aglycon.

Concise synthesis of the tetrasaccharide repeating unit of the O-antigen from Escherichia coli O131 containing N-acetyl neuraminic acid.

Synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O131 was accomplished through a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The challenging α-glycosylation of N-acetyl neuraminic acid was achieved through activation of thioglycoside using NIS-mediated glycosylation strategy.

Chemical synthesis of the pentasaccharide related to the anti-inflammatory oleanane type saponins isolated from medicinal plant Aster tataricus L. f.

Total synthesis of the pentasaccharide related to the saponin isolated from the medicinal plant Aster tataricus L. f. is reported in the form of its allyl glycoside.

1,6-heptadiynes based cyclopolymerization functionalized with mannose by post polymer modification for protein interaction.

Carbohydrate functionalized polymers or Glycopolymers have earned a great deal of interest in recent times for their potential biomedical applications. In the present study, a mannose containing glycopolymer was synthesized by cyclopolymerization of malonic acid derivative using second generation Hoveyda Grubbs' catalyst. Post-polymerization modification was done to install a propargyl moiety.

A brief insight to the role of glyconanotechnology in modern day diagnostics and therapeutics.

Carbohydrate-protein and carbohydrate-carbohydrate interactions are very important for various biological processes. Although the magnitude of these interactions is low compared to that of protein-protein interaction, the magnitude can be boosted by multivalent approach known as glycocluster effect. Nanoparticle platform is one of the best ways to present diverse glycoforms in multivalent manner and thus, the field of glyconanotechnology has emerged as an important field of research considering their potential applications in diagnostics and therapeutics.

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Ruminococcus gnavus.

Microorganisms present in the guts are the causative agents for various diseases in humans. More and more studies are correlating such diseases and the responsible microorganism. The Gram-positive bacterium Ruminococcus gnavus (R.

Chemical Synthesis of β-l-Rhamnose Containing the Pentasaccharide Repeating Unit of the -Specific Polysaccharide from a Halophilic Bacterium RU5S2EL in the Form of Its 2-Aminoethyl Glycoside.

Total synthesis of the pentasaccharide repeating unit of the OPS from RU5S2EL is accomplished through a [3+2] block strategy. Picoloyl-induced hydrogen-bond-assisted aglycon delivery (HAD) is used for two consecutive 1,2--l-rhamnosylations, and remote participation is used for α-selective glucosylation. The choice of 2-aminoethyl glycoside at the reducing end is opted for, leaving the scope for further glycoconjugate formation without hampering the reducing-end stereochemistry.

Chemical synthesis of the rare D-Fuc3NAc containing tetrasaccharide repeating unit of the O-antigenic polysaccharide from E. coli O74.

Chemical synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O74 is accomplished by a convergent [2 + 2] block synthesis strategy. The challenging rare D-Fuc3NAc has been prepared using DTBP and TIPST mediated deoxygenation reaction.

Edible marine algae: a new source for anti-mycobacterial agents.

Tuberculosis is a dreaded disease, which causes innumerable death worldwide. The emergence of drug resistance strains makes the situation devastating. Therefore, for better management of public health, it is mandatory to search for new anti-mycobacterial agents.

Synthesis of the tetrasaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100 having rare D-Quip3NAc.

Chemical synthesis of the complex tetrasaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100 is accomplished in the form of its 2-aminoethyl glycoside to leave the scope for further glycoconjugate formation without hampering the anomeric stereochemistry. A [2 + 2] strategy is followed to complete the total synthesis and a late stage TEMPO mediated oxidation is used to install the required uronic acid. A radical mediated 6-deoxygenation with subsequent protecting group manipulation strategy is used for the preparation of the rare D-FucpNAc and D-Quip3NAc derivatives from suitable d-glucosamine derivatives.

Synthesis of the pentasaccharide repeating unit of the O-antigen from C4115 containing the rare α-d-FucNAc.

Total synthesis of the pentasaccharide repeating unit associated with the O-antigen of C4115 is reported. The synthesis of the said oligosaccharide was accomplished through rational protecting group manipulations on commercially available monosaccharides followed by stereoselective glycosylations either by activation of thioglycosides or glycosyl trichloroacetimidates and was found to be productive. Towards the synthesis of the rare sugar unit, α-d-FucNAc in this case, it was established that the methoxymethyl (MOM) group is advantageous over the earlier reported tetrahydro pyran (THP) protection.

Chemical synthesis of the pentasaccharide repeating unit of the -specific polysaccharide from O132 in the form of its 2-aminoethyl glycoside.

The total chemical synthesis of the pentasaccharide repeating unit of the -polysaccharide from O132 is accomplished in the form of its 2-aminoethyl glycoside. The 2-aminoethyl glycoside is particularly important as it allows further glycoconjugate formation utilizing the terminal amine without affecting the stereochemistry of the reducing end. The target was achieved through a [3 + 2] strategy where the required monosaccharide building blocks are prepared from commercially available sugars through rational protecting group manipulation.

Concise chemical synthesis of the pentasaccharide repeating unit of the O-antigen from Escherichia albertii O2.

Total chemical synthesis of the pentasaccharide repeating unit of the O-antigen from Escherichia albertii O2 is accomplished by following a [3 + 2] strategy. The target pentasaccharide in the form of its 2-aminoethyl glycoside is particularly attractive as the free amine end can be coupled with suitable aglycon to make further glycoconjugate without affecting the anomeric stereochemistry. Phthalimido derivatives were used successfully as the precursor of the desired acetamido glucose moieties and ensured the 1,2-trans linkages.

Chemical synthesis of the 4-amino-4,6-dideoxy-d-glucose containing pentasaccharide repeating unit of the O-specific polysaccharide from Aeromonas hydrophila strain K691 in the form of its 2-aminoethyl glycoside.

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Aeromonas hydrophilastrain K691 is reported. Synthesis of the pentasaccharide is accomplished by using a common disaccharide in sequence and finally attaching the rare sugar unit. The target structure was made in the form of its 2-aminoethyl glycoside which is essential for further glycconjugate formation.

Synthesis of the tetrasaccharide related to the repeating unit of the O-antigen from Azospirillum brasilense Jm125A2 in the form of its 2-aminoethyl glycoside.

Total chemical synthesis of the linear tetrasaccharide repeating unit β-D-Glc-(1 → 2)-α-L-Rha-(1 → 3)-α-L-Rha-(1 → 2)-α-L-Rha-CHCHNH of the O-antigen from Azospirillum brasilense Jm125A2 is accomplished through rational protecting group manipulations of commercially available monosaccharides and stereoselective glycosylations. The target tetrasaccharide in the form of its 2-aminoethyl glycoside is obtained in ∼24% yield over 10 steps following a linear strategy. The structure is particularly suitable for further glycoconjugate formation through the terminal free amine without hampering the reducing end stereochemistry.

Distinct Mechanoresponsive Luminescence, Thermochromism, Vapochromism, and Chlorine Gas Sensing by a Solid-State Organic Emitter.

In this study, we report a synthetically simple donor-acceptor (D-A)-type organic solid-state emitter that displays unique fluorescence switching under mechanical stimuli. Orange and yellow emissive crystals of (, ) exhibit an unusual "back and forth" fluorescence response to mechanical force. Gentle crushing (mild pressure) of the orange or yellow emissive crystal results in hypsochromic shift to cyan emissive fragments (λ = 498-501 nm) with a large wavelength shift Δλ = -71 to -96 nm, while further grinding results in bathochromic swing to green emissive powder λ = 540-550 nm, Δλ = +40 to 58 nm.

Chemical O-Glycosylations: An Overview.

The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo- and regioselectivity through the formation of glycosidic bonds.

A Selective Galactose-Coumarin-Derived Galectin-3 Inhibitor Demonstrates Involvement of Galectin-3-glycan Interactions in a Pulmonary Fibrosis Model.

Synthesis of doubly 3-O-coumarylmethyl-substituted thiodigalactosides from bis-3-O-propargyl-thiodigalactoside resulted in highly selective and high affinity galectin-3 inhibitors. Mutant studies, structural analysis, and molecular modeling revealed that the coumaryl substituents stack onto arginine side chains. One inhibitor displayed efficacy in a murine model of bleomycin-induced lung fibrosis similar to that of a known nonselective galectin-1/galectin-3 inhibitor, which strongly suggests that blocking galectin-3 glycan recognition is an important antifibrotic drug target.

Linear synthesis of the hexasaccharide related to the repeating unit of the O-antigen from Shigella flexneri serotype 1d (I: 7,8).

Total synthesis of the hexasaccharide repeating unit of the O-antigen from Shigella flexneri serotype 1d (I: 7,8), α-D-Glcp-(1→3)-α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-β-D-GlcpNAc, is reported by following a linear strategy. The target hexasaccharide was synthesized by sequential glycosylations of suitably protected monosaccharide derivatives prepared from commercially available monosaccharides through rational protecting group manipulations. Stereoselective glycosylations were accomplished by the activation of thioglycoside using N-iodosuccinimide and H2SO4-silica.

Isolation of phenazine 1,6-di-carboxylic acid from Pseudomonas aeruginosa strain HRW.1-S3 and its role in biofilm-mediated crude oil degradation and cytotoxicity against bacterial and cancer cells.

Pseudomonas sp. has long been known for production of a wide range of secondary metabolites during late exponential and stationary phases of growth. Phenazine derivatives constitute a large group of secondary metabolites produced by microorganisms including Pseudomonas sp.

Chemical synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Azospirillum brasilense SR80.

A linear strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-polysaccharide from Azospirillum brasilense SR80. Stepwise glycosylation of the rationally protected thioglycoside donors activated by NIS in the presence of La(OTf)3 furnished the target tetrasaccharide. The glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and afforded the required derivatives in good to excellent yields.

Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain.

A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields.