Review
Biotechnology & Applied Microbiology
Tomohiko Matsuzawa, Akira Watanabe, Takahiro Shintani, Katsuya Gomi, Katsuro Yaoi
Summary: Aspergillus species are closely associated with humanity through fermentation, infectious disease, and mycotoxin contamination of food. This review focuses on the machinery of the xyloglucan degradation in Aspergillus species using glycoside hydrolases, emphasizing the crucial role of cooperative actions of these enzymes.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2021)
Article
Biotechnology & Applied Microbiology
Tomohiko Matsuzawa, Masahiro Watanabe, Yusuke Nakamichi, Akihiko Kameyama, Naoshi Kojima, Katsuro Yaoi
Summary: In this study, an extracellular alpha-xylosidase, AxyB, was identified and characterized in Aspergillus oryzae, belonging to glycoside hydrolase family 31 and involved in releasing D-xylose from xyloglucan oligosaccharides. The research shows that AxyB plays a key role in the degradation of xyloglucans by releasing the xylopyranosyl side chain from these oligosaccharides.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Organic
Samim Sahaji, Pradip Shit, Anup Kumar Misra
Summary: The octasaccharide repeating unit of the K55 capsular polysaccharide of Acinetobacter baumannii BAL_204 strain was successfully synthesized using a convergent [5+3] block glycosylation strategy. Sequential stereoselective glycosylations were employed to synthesize the pentasaccharide and trisaccharide components. The temporary alkyl protecting group, p-methoxybenzyl (PMB), was removed under thiophilic glycosylation conditions by raising the temperature. A late-stage TEMPO-mediated selective oxidation allowed the incorporation of the D-glucuronic acid moiety in the octasaccharide. N-iodosuccinimide (NIS) and perchloric acid over silica (HClO4-SiO2) were used as a thiophilic promoter for thioglycoside activation. HClO4-SiO2 also served as a solid acid activator for glycosyl trichloroacetimidate derivative.
SYNTHESIS-STUTTGART
(2023)
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, Physical
Oluwafemi Akintola, Weiwu Ren, Pal John Pal Adabala, Sandeep Bhosale, Yang Wang, Yumeela Ganga-Sah, Robert Britton, Andrew J. Bennet
Summary: The study explores hydrolyses of cyclohexenyl-based carbasugars by two Bacteroides thetaiotaomicron enzymes, showing that they yield nucleophilic substitutions at the pseudoanomeric center of the substrates with significantly different linear energy relationships. Kinetic data reveal distinct mechanisms and reaction rates for the inverting alpha-glucosidase and retaining alpha-galactosidase.
Review
Biochemistry & Molecular Biology
Gabriel G. Jimenez, Alexandra G. Duran, Francisco A. Macias, Ana M. Simonet
Summary: Yucca is a major source of steroidal saponins, with a total of 108 saponins from eight species of the genus described in a recent review. LC-MS technique is commonly used for evaluation and quality control, but further methods are needed for routine analysis of commercial preparations. Most studies so far have focused on Y. schidigera extract, indicating that the identification of saponins in the Yucca genus remains a unresolved question.
Article
Chemistry, Applied
Mai Dinh Tri, Tran Thi Mai Tram, Le Hoang Ngoc, Tran Nguyen Minh An, Nguyen Tan Phat, Phan Nhat Minh, Nguyen Van Kieu, Dang Van Son, Thi-Phuong Nguyen, Tran Thi Ngoc Mai, Thuc-Huy Duong
Summary: A new glycoside, recurvataside (1), and six known compounds were isolated from Mussaenda recurvata. Recurvataside is the first occurrence of a delta-oleanolic acid saponin bearing two D-glucose units at C-3 and C-28 in nature, and the first time a delta-oleanane-type saponin has been reported in the genus Mussaenda. The compounds were evaluated for their cytotoxicity against two cancer cell lines, with only compound 7 exhibiting moderate activity. Additionally, the compounds showed significant reduction of nitrite accumulation in LPS-stimulated RAW 264.7 cells.
NATURAL PRODUCT RESEARCH
(2023)
Article
Biochemistry & Molecular Biology
Jianfa Wu, Lei Li, Chang Liu, Chunyi Li, Ying Cui, Weixing Ding, Jing Zhang, Leiling Shi
Summary: Two new compounds were isolated from Allii Macrostemonis Bulbus, named 4,4'-bis(β-D-glucopyranosyloxy)biphenyl and spirostane-25(27)-en-2α,3β-diol-3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside. Alongside these, ten known compounds were identified. The structures of all compounds were confirmed using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D, and 2D NMR spectroscopy. Some of the compounds showed strong antioxidant activity. The discovery of these new compounds is important for identifying quality markers and exploring novel natural antioxidants.
Article
Chemistry, Applied
Zhao Zhao, Hanqi Cui, Xianheng Wang, Jianyong Zhang, Changkuo Zhao
Summary: A convenient method has been developed for glycol-conjugation in the 3-position of beta-anhydroicaritine, with reasonable yield. The correct structure of the 3-glycosylated beta-anhydroicaritine derivatives was confirmed through H-1 NMR, C-13 NMR, and HRMS spectroscopy. These compounds have lower solubility than icaritin but higher solubility than icariside II in CCl4. Screening results showed that compounds 12h, 12i, and 12j exhibited higher cytotoxicity to HepG2 and MCF-7 cells at a concentration of 50 μM.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Applied
Guanchen Liu, Jingjing Shen, Yaoguang Chang, Xuanwei Mei, Guangning Chen, Yuying Zhang, Changhu Xue
Summary: A new bacterial enzyme, Fun174A, was discovered to degrade sulfated fucans in sea cucumbers, exhibiting significant biological and biomedical activities.
CARBOHYDRATE POLYMERS
(2023)
Article
Agriculture, Multidisciplinary
Zhen Qin, Sainan Yu, Kemin Zhang, Xiasen Wei, Junjie Li, Zheyi Zhang, Sibao Wan, Haiyan Gao
Summary: In this study, a β-1,3-glucanase named BsGlc157A was identified from Bacteroides sp. M27. It exhibited optimal catalytic activity at pH 6.0 and 40 degrees C. BsGlc157A adopted a classic (beta/alpha)(8) TIM-barrel structure and two catalytic residues were confirmed. Moreover, BsGlc157A showed inhibitory effects on the hyphal growth of fruit pathogenic fungi, highlighting its potential as a biocontrol agent.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Zhen Qin, Sainan Yu, Kemin Zhang, Xiasen Wei, Junjie Li, Zheyi Zhang, Sibao Wan, Haiyan Gao
Summary: In this study, a GH family 157 endo-beta-1,3-glucanase (BsGlc157A) was identified and characterized from Bacteroides sp. M27. It was found to have applications in fields such as food processing, plant protection, and breweries. The study also revealed its catalytic properties and antifungal activity.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Organic
Swapan Kumar Jana, Samim Sahaji, Pradip Shit, Anup Kumar Misra
Summary: A synthetic strategy involving challenging stereoselective glycosylation steps was used to successfully synthesize the hexasaccharide repeating unit corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 7A.
SYNTHESIS-STUTTGART
(2023)
Article
Medicine, Research & Experimental
Maria L. Jaramillo, Traian Sulea, Yves Durocher, Mauro Acchione, Melissa J. Schur, Anna Robotham, John F. Kelly, Marie-France Goneau, Alma Robert, Yuneivy Cepero-Donates, Michel Gilbert
Summary: Effective processes for synthesizing antibody-drug conjugates (ADCs) require site-specific incorporation of the payload, optimal drug/antibody ratio, and a homogeneous product. Conventional ADCs often face issues like interference with epitope binding and product heterogeneity. This study presents a more controlled process where the drug is specifically conjugated to Fab N-linked glycans, resulting in ADCs with desired drug/antibody ratio and efficient targeting.
Article
Chemistry, Analytical
Sherouk Hussein Sweilam, Maha B. O. Ebrahim, Mehnaz Kamal, El-Sayed Khafagy, Ashraf N. Abdalla, Mohamed E. Elzubier, Ehssan H. Moglad
Summary: Combretaceae plants, especially Combretum glutinosum Perr. Ex Dc., have been traditionally used in Sudanese cultures for their medicinal properties. In this study, six compounds were isolated from the ethyl acetate extract of C. glutinosum, including a new flavonoid compound and five known compounds. These compounds showed cytotoxic activities against breast, colon, liver, and lung cancer cell lines, with compounds 1 and 6 exhibiting the highest cytotoxicity. Furthermore, compounds 1 and 3 demonstrated the ability to induce apoptosis and perturb the cell cycle in MCF7 cells.
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