Article
Chemistry, Organic
Samim Sahaji, Pradip Shit, Anup Kumar Misra
Summary: A convergent [4+2] stereoselective block glycosylation strategy was developed for the synthesis of the hexasaccharide repeating unit of Klebsiella K19 strain's capsular polysaccharide with high yield. Temporary alkyl protecting group p-methoxybenzyl (PMB) was used and removed through glycosylation conditions. Thioglycoside served as a glycosyl acceptor in an orthogonal glycosylation reaction. TEMPO-mediated selective oxidation and thiophilic promoter N-iodosuccinimide (NIS) in combination with perchloric acid supported over silica (HClO4-SiO2) were used.
SYNTHESIS-STUTTGART
(2023)
Article
Biochemistry & Molecular Biology
Anirban Bera, Balaram Mukhopadhyay
Summary: The total synthesis of the pentasaccharide repeating unit of the exopolysaccharide from Lactobacillus rhamnosus BIM B-1039 was successfully achieved. This was done through bis-glycosylation on a suitably protected trisaccharide di-ol, introducing the stereochemically challenging beta-D-ManNAc residue and forming the desired mannosamine moiety by inversion of the 2-OH position with azido group. The strategy of using p-methoxyphenyl glycoside at the reducing end was found to open up the possibility of further conjugation with suitable aglycon.
CARBOHYDRATE RESEARCH
(2022)
Article
Biochemistry & Molecular Biology
Tanmoy Halder, Sunil K. Yadav, Somnath Yadav
Summary: Synthetic conjugate vaccines are crucial in preventing Gram-negative bacterial diseases. This study reports the synthesis of the trisaccharide repeating unit of S. maltophilia O6 antigen, which provides a potential candidate for vaccine synthesis.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Organic
Tanmoy Halder, Somnath Yadav
Summary: The synthesis of the trisaccharide repeating unit of P. stuartii O49 serotype O-antigen polysaccharide has been successfully achieved, laying the foundation for the development of vaccines against this pathogen.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Debasish Pal, Balaram Mukhopadhyay
Summary: The total synthesis of the pentasaccharide repeating unit from Halomonas ventosae RU5S2EL OPS is achieved through a [3+2] block strategy. Utilizing specific methods for rhamnosylation and glucosylation, as well as opting for 2-aminoethyl glycoside at the reducing end, allows for further glycoconjugate formation without affecting the reducing-end stereochemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Anirban Adak, Sakshi Balasaria, Balaram Mukhopadhyay
Summary: The synthesis of the tetrasaccharide repeating unit of E. coli O131 O-antigen was achieved using a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The challenging alpha-glycosylation of N-acetyl neuraminic acid was successfully accomplished through the activation of thioglycoside using NIS-mediated glycosylation strategy. The resulting tetrasaccharide in 3-aminopropyl glycoside form can be utilized for further glycoconjugate formation without affecting the anomeric stereochemistry.
CARBOHYDRATE RESEARCH
(2022)
Article
Biotechnology & Applied Microbiology
Goutam Mukherjee, Balaram Mukhopadhyay, Alok Kumar Sil
Summary: The study investigated two edible marine algae, Ulva lactuca and Ulva intestinalis, and found that their extracts have anti-mycobacterial activity, inhibit biofilm formation, and disperse preformed biofilms. These extracts also enhance the activity of isoniazid and rifampicin, potentially providing effective treatment against mycobacterial diseases.
FOLIA MICROBIOLOGICA
(2021)
Article
Biochemistry & Molecular Biology
Debasish Pal, Mrinal Naskar, Anirban Bera, Balaram Mukhopadhyay
Summary: This study investigates the role of the Gram-positive bacterium Ruminococcus gnavus (R. gnavus) in causing symptoms of Crohn's disease. The chemical synthesis of the pentasaccharide repeating unit of O-polysachharide produced by R. gnavus is described, with the challenge being the presence of two consecutive 1,2-cis glucose units. Successful 1,2-cis glycosylation of glucose is achieved with excellent yield through rational protecting group manipulation and activation of thioglycosides at -20 degrees C.
CARBOHYDRATE RESEARCH
(2021)
Article
Biochemistry & Molecular Biology
Rituparna Das, Balaram Mukhopadhyay
Summary: Carbohydrate-protein and carbohydrate-carbohydrate interactions are crucial for biological processes, with the potential to be boosted by the multivalent glycocluster effect. Researchers have made significant progress in the field of glyconanotechnology by utilizing nanoparticle platforms to present diverse glycoforms and exploring their applications in diagnostics and therapeutics.
CARBOHYDRATE RESEARCH
(2021)
Article
Biochemistry & Molecular Biology
Anirban Bera, Balaram Mukhopadhyay
Summary: The chemical synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O74 is achieved through a convergent [2 + 2] block synthesis strategy involving the preparation of the rare D-Fuc3NAc and other monosaccharide synthons, as well as stereoselective glycosylations. The target tetrasaccharide is synthesized in the form of its 2-aminoethyl glycoside to allow for further glycoconjugate formation without altering the anomeric stereochemistry.
CARBOHYDRATE RESEARCH
(2021)
Article
Chemistry, Organic
Debasish Pal, Balaram Mukhopadhyay
Summary: The total synthesis of the pentasaccharide repeating unit from Halomonas ventosae RU5S2EL OPS is achieved through a [3+2] block strategy. Utilizing specific methods for rhamnosylation and glucosylation, as well as opting for 2-aminoethyl glycoside at the reducing end, allows for further glycoconjugate formation without affecting the reducing-end stereochemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Pawan Kumar, Pintu Kanjilal, Rituparna Das, Tapan K. Dash, Manikandan Mohanan, Trong-Nghia Le, N. Vijayakameswara Rao, Balaram Mukhopadhyay, Raja Shunmugam
Summary: Carbohydrate functionalized polymers, particularly Glycopolymers, have attracted significant attention for their potential biomedical applications. In this study, a mannose-containing glycopolymer was successfully synthesized and characterized, demonstrating self-assembly into different morphologies in water and DMSO. Interaction with Con A resulted in increased fluorescence, while in vitro cytotoxicity studies showed low toxicity at high concentrations on MCF 7 cell line.
CARBOHYDRATE RESEARCH
(2021)
Article
Biochemistry & Molecular Biology
Madhumita Bera, Balaram Mukhopadhyay
Summary: The total synthesis of a pentasaccharide related to the saponin from Aster tataricus L. f. has been achieved by using a [3 + 2] block synthesis strategy. The trisaccharide acceptor and disaccharide donor were obtained through stereoselective glycosylations from semi-protected monosaccharides. The synthesized pentasaccharide will be useful for further biological evaluation and potential glycoconjugate formation.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Organic
Debasish Pal, Aritra Chaudhury, Balaram Mukhopadhyay
Summary: This manuscript reports the chemical synthesis method of the trisaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100. The challenging residues were successfully incorporated through rational protecting group manipulations and a linear strategy, and the desired carboxylic acid moiety was introduced through TEMPO-mediated oxidation. The use of aminoethyl glycoside allows further glycoconjugate formation without affecting the anomeric stereochemistry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Anirban Adak, Sakshi Balasaria, Balaram Mukhopadhyay
Summary: The synthesis of the tetrasaccharide repeating unit of E. coli O131 O-antigen was achieved using a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The challenging alpha-glycosylation of N-acetyl neuraminic acid was successfully accomplished through the activation of thioglycoside using NIS-mediated glycosylation strategy. The resulting tetrasaccharide in 3-aminopropyl glycoside form can be utilized for further glycoconjugate formation without affecting the anomeric stereochemistry.
CARBOHYDRATE RESEARCH
(2022)
Article
Biochemistry & Molecular Biology
Anirban Bera, Balaram Mukhopadhyay
Summary: The total synthesis of the pentasaccharide repeating unit of the exopolysaccharide from Lactobacillus rhamnosus BIM B-1039 was successfully achieved. This was done through bis-glycosylation on a suitably protected trisaccharide di-ol, introducing the stereochemically challenging beta-D-ManNAc residue and forming the desired mannosamine moiety by inversion of the 2-OH position with azido group. The strategy of using p-methoxyphenyl glycoside at the reducing end was found to open up the possibility of further conjugation with suitable aglycon.
CARBOHYDRATE RESEARCH
(2022)
Article
Biochemistry & Molecular Biology
Sakshi Balasaria, Balaram Mukhopadhyay
Summary: In this study, we chemically synthesized the pentasaccharide repeating unit of E. coli strain SDLZB008's O-antigen using a linear strategy that involved rationally protected monosaccharide derivatives to ensure the desired stereochemistry. We incorporated a 2-aminoethyl glycoside at the reducing end of the pentasaccharide, allowing the terminal free amine to be used for further conjugation without affecting the stereochemistry at the reducing end. Additionally, we successfully incorporated the rare D-Fucp3NAc moiety using a 3-azido derivative derived from a known 3-azido quinovose derivative.
CARBOHYDRATE RESEARCH
(2023)
Article
Materials Science, Multidisciplinary
Priyadarsi De, Subhasish Sahoo, Soumya Paul, Swagata Pan, Debasish Pal, Shubham Das, Sankar Maiti, Balaram Mukhopadhyay, Paolo Tecilla
Summary: A multifunctional macromolecular architecture with alternating cholic acid (CA) and glucose pendants was synthesized. The resulting copolymers self-assembled into micellar nanoscaffolds with hydrophobic cores and sugar-coated shells. These nanoparticles encapsulated hydrophobic molecules, exhibited inherent fluorescence, formed inclusion complexes with β-cyclodextrin, and recognized Concanavalin A.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Organic
Anirban Adak, Madhumita Bera, Balaram Mukhopadhyay
Summary: This paper reports the chemical synthesis of the hexasaccharide repeating unit associated with the exopolysaccharide of Lactobacillus mucosae VG1. The total synthesis was achieved through a convergent [2 + 2 + 2] strategy using rationally protected monosaccharide derivatives. Chemoselective activation of glycosyl donors and regioselective nucleophilicity of acceptors were successfully employed throughout the chemical synthesis.
Article
Materials Science, Multidisciplinary
Subhasish Sahoo, Soumya Paul, Swagata Pan, Debasish Pal, Shubham Das, Sankar Maiti, Balaram Mukhopadhyay, Paolo Tecilla, Priyadarsi De
Summary: This article reports the design and synthesis of a multifunctional macromolecular architecture with alternating cholic acid and glucose pendants. The architecture was prepared through reversible addition-fragmentation chain-transfer copolymerization using a polyethylene glycol-conjugated chain transfer agent. The resulting copolymers formed self-assembled micellar nanoscaffolds in aqueous media, encapsulated hydrophobic molecules, formed inclusion complexes with β-cyclodextrin, and recognized Concanavalin A. The study offers a simple way to prepare a multifunctional alternating copolymer with various capabilities.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Aritra Chaudhury, Balaram Mukhopadhyay
