Convergent synthesis of a hexadecavalent heterobifunctional ABO blood group glycoconjugate
Carbohydr Res. 2023 Nov 23;535:108988. doi: 10.1016/j.carres.2023.108988. Online ahead of print.ABSTRACTNaturally occurring glycans are often found in a multivalent presentation. Cell surface receptors that recognize these displays may form clusters, which can lead to signalling or endocytosis. One of the challenges in generating synthetic displays of multivalent carbohydrates is providing high valency as well as access to heterofunctional conjugates to allow attachment of multiple antigens or payloads. We designed a strategy based on a set of bifunctional linkers to generate a heterobifunctional multivalent display of two...
Source: Carbohydrate Research - December 4, 2023 Category: Genetics & Stem Cells Authors: Gour Chand Daskhan Hanh-Thuc Ton Tran Christopher W Cairo Source Type: research

Xylarcurcosides A-C, three novel isopimarane-type diterpene glycosides from Xylaria curta YSJ-5
Carbohydr Res. 2023 Nov 23;535:108987. doi: 10.1016/j.carres.2023.108987. Online ahead of print.ABSTRACTThree previously undescribed isopimarane-type diterpene glycosides named as xylarcurcosides A-C (1-3) along with two known ones 16-α-d-mannopyranosyloxyisopimar-7-en-19-oic acid (4) and hypoxylonoid A (5) were successfully isolated from an ethyl acetate extract of the endophytic fungus Xylaria curta YSJ-5 growing in leaves of Alpinia zerumbet. The spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction experiments were conducted to identify their absolute chemical structures. All t...
Source: Carbohydrate Research - December 4, 2023 Category: Genetics & Stem Cells Authors: Shanshan Wei Chen Chen Jiaying Lai Yanjiang Zhang Xinmiao Nong Fangfang Duan Ping Wu Sasa Wang Haibo Tan Source Type: research

Isolation and structural characterization of eight new resin glycosides, calyhedins XVI-XXIII, from the rhizomes of Calystegia hederacea
In this study, eight new resin glycosides, termed calyhedins XVI (1)-XXIII (8), were isolated from the rhizomes of C. hederacea. Compounds 1-8 are penta- or hexa-glycosides with macrolactone structures, and their sugar moieties are partially acylated by five organic acids, including 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R-methyl-3R-hydroxybutyric acids. Compounds 1-5 are the first identified macrocyclic resin glycosides with five monosaccharides obtained from this plant, and 2 and 4 are the first to be characterized as containing calyhedic acid A as the glycosidic acid component. Compounds 1-8 were of the four fo...
Source: Carbohydrate Research - December 4, 2023 Category: Genetics & Stem Cells Authors: Masateru Ono Ryota Arakawa Hirotaka Nishikawa Nodoka Misuda Shin Yasuda Hitoshi Yoshimitsu Ryota Tsuchihasi Masafumi Okawa Junei Kinjo Source Type: research

Convergent synthesis of a hexadecavalent heterobifunctional ABO blood group glycoconjugate
Carbohydr Res. 2023 Nov 23;535:108988. doi: 10.1016/j.carres.2023.108988. Online ahead of print.ABSTRACTNaturally occurring glycans are often found in a multivalent presentation. Cell surface receptors that recognize these displays may form clusters, which can lead to signalling or endocytosis. One of the challenges in generating synthetic displays of multivalent carbohydrates is providing high valency as well as access to heterofunctional conjugates to allow attachment of multiple antigens or payloads. We designed a strategy based on a set of bifunctional linkers to generate a heterobifunctional multivalent display of two...
Source: Carbohydrate Research - December 4, 2023 Category: Genetics & Stem Cells Authors: Gour Chand Daskhan Hanh-Thuc Ton Tran Christopher W Cairo Source Type: research

Molecular weight-dependent antitumor effects of prunes-derived type I arabinogalactan on human and murine triple wild-type melanomas
Carbohydr Res. 2023 Nov 22;535:108986. doi: 10.1016/j.carres.2023.108986. Online ahead of print.ABSTRACTThe regulation of metastasis-related cellular aspects of two structurally similar AGIs from prunes tea infusion, with different molar masses, was studied in vitro against Triple Wild-Type metastatic melanoma (TWM) from murine and human origin. The higher molar mass AGI (AGI-78KDa) induced TWMs cells death and, in murine cell line, it decreased some metastasis-related cellular processes: invasiveness capacity, cell-extracellular matrix interaction, and colonies sizes. The lower molar mass AGI (AGI-12KDa) did not induce ce...
Source: Carbohydrate Research - December 2, 2023 Category: Genetics & Stem Cells Authors: Keila Taiana Vaz da Luz Jenifer Pendiuk Gon çalves Daniel de Lima Bellan Bruna Renata Caitano Visnheski Vanessa Suzane Schneider Lucimara Mach Cortes Cordeiro Jos é Eduardo Vargas Renato Puga Edvaldo da Silva Trindade Carolina Camargo de Oliveira Fernan Source Type: research

Molecular weight-dependent antitumor effects of prunes-derived type I arabinogalactan on human and murine triple wild-type melanomas
Carbohydr Res. 2023 Nov 22;535:108986. doi: 10.1016/j.carres.2023.108986. Online ahead of print.ABSTRACTThe regulation of metastasis-related cellular aspects of two structurally similar AGIs from prunes tea infusion, with different molar masses, was studied in vitro against Triple Wild-Type metastatic melanoma (TWM) from murine and human origin. The higher molar mass AGI (AGI-78KDa) induced TWMs cells death and, in murine cell line, it decreased some metastasis-related cellular processes: invasiveness capacity, cell-extracellular matrix interaction, and colonies sizes. The lower molar mass AGI (AGI-12KDa) did not induce ce...
Source: Carbohydrate Research - December 2, 2023 Category: Genetics & Stem Cells Authors: Keila Taiana Vaz da Luz Jenifer Pendiuk Gon çalves Daniel de Lima Bellan Bruna Renata Caitano Visnheski Vanessa Suzane Schneider Lucimara Mach Cortes Cordeiro Jos é Eduardo Vargas Renato Puga Edvaldo da Silva Trindade Carolina Camargo de Oliveira Fernan Source Type: research

Convergent synthesis of functionalized derivatives of stage-specific embryonic antigens 3 & amp; 4
Carbohydr Res. 2023 Nov 25;535:108990. doi: 10.1016/j.carres.2023.108990. Online ahead of print.ABSTRACTStage-specific embryonic antigens (SSEAs) are carbohydrate markers that have diverse roles in embryonic development. However, the exact roles of SSEAs remain unclear. To obtain mechanistic insights into their roles, we aimed to develop functionalized SSEA glycan analogs via chemical synthesis. Herein, we report a convergent synthetic approach for SSEA-3 and SSEA-4 analogs using readily available versatile building blocks. A key step, namely the stereoselective glycosylation of a common tetrasaccharide acceptor, was succe...
Source: Carbohydrate Research - December 1, 2023 Category: Genetics & Stem Cells Authors: Rita Pal Ayano Yamazaki Naoko Komura Hide-Nori Tanaka Akihiro Imamura Hideharu Ishida Hiromune Ando Source Type: research

Convergent synthesis of functionalized derivatives of stage-specific embryonic antigens 3 & amp; 4
Carbohydr Res. 2023 Nov 25;535:108990. doi: 10.1016/j.carres.2023.108990. Online ahead of print.ABSTRACTStage-specific embryonic antigens (SSEAs) are carbohydrate markers that have diverse roles in embryonic development. However, the exact roles of SSEAs remain unclear. To obtain mechanistic insights into their roles, we aimed to develop functionalized SSEA glycan analogs via chemical synthesis. Herein, we report a convergent synthetic approach for SSEA-3 and SSEA-4 analogs using readily available versatile building blocks. A key step, namely the stereoselective glycosylation of a common tetrasaccharide acceptor, was succe...
Source: Carbohydrate Research - December 1, 2023 Category: Genetics & Stem Cells Authors: Rita Pal Ayano Yamazaki Naoko Komura Hide-Nori Tanaka Akihiro Imamura Hideharu Ishida Hiromune Ando Source Type: research

Expedient synthesis of l-heptose derived septacidin building blocks from l-glucose
Carbohydr Res. 2023 Nov 20;534:108985. doi: 10.1016/j.carres.2023.108985. Online ahead of print.ABSTRACTBacterial natural products containing heptosides such as septacidin represent interesting scaffolds for the development of drugs to combat antimicrobial resistance. However, very few synthetic strategies have been reported to grant access to these derivatives. Here, we have devised a synthetic pathway to l-glycero-l-glucoheptoside, a key building block en route to septacidin, directly from l-glucose. Importantly, we show that carbon homologation at C6, encompassing oxidation of the C6-OH followed by methylenation, is sig...
Source: Carbohydrate Research - November 28, 2023 Category: Genetics & Stem Cells Authors: Debashis Dhara Laurence A Mulard Marcel Hollenstein Source Type: research

Reinvestigation of SnCl < sub > 4 < /sub > catalyzed efficient synthesis of 2,3-unsaturated glycopyranosides
Carbohydr Res. 2023 Nov 23;534:108989. doi: 10.1016/j.carres.2023.108989. Online ahead of print.ABSTRACTThe Ferrier rearrangement is a powerful tool to prepare 2,3-unsaturated glycopyranosides. We have reinvestigated SnCl4 catalyzed Ferrier rearrangements through direct allylic substitution of the hydroxyl group at the C-3 position of glycals, resulting in the formation of stereoselective 2,3-unsaturated glycosides at 0 °C. The catalytic amount of SnCl4 (0.1 equiv.) was successfully used to promote this transformation on 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal and 3,4-di-O-acetyl-D-arabinal using variou...
Source: Carbohydrate Research - November 28, 2023 Category: Genetics & Stem Cells Authors: Yogesh Yadav Rajdeep Tyagi Kanchan Yadav Ghanshyam Tiwari Ram Sagar Source Type: research

Expedient synthesis of l-heptose derived septacidin building blocks from l-glucose
Carbohydr Res. 2023 Nov 20;534:108985. doi: 10.1016/j.carres.2023.108985. Online ahead of print.ABSTRACTBacterial natural products containing heptosides such as septacidin represent interesting scaffolds for the development of drugs to combat antimicrobial resistance. However, very few synthetic strategies have been reported to grant access to these derivatives. Here, we have devised a synthetic pathway to l-glycero-l-glucoheptoside, a key building block en route to septacidin, directly from l-glucose. Importantly, we show that carbon homologation at C6, encompassing oxidation of the C6-OH followed by methylenation, is sig...
Source: Carbohydrate Research - November 28, 2023 Category: Genetics & Stem Cells Authors: Debashis Dhara Laurence A Mulard Marcel Hollenstein Source Type: research

Reinvestigation of SnCl < sub > 4 < /sub > catalyzed efficient synthesis of 2,3-unsaturated glycopyranosides
Carbohydr Res. 2023 Nov 23;534:108989. doi: 10.1016/j.carres.2023.108989. Online ahead of print.ABSTRACTThe Ferrier rearrangement is a powerful tool to prepare 2,3-unsaturated glycopyranosides. We have reinvestigated SnCl4 catalyzed Ferrier rearrangements through direct allylic substitution of the hydroxyl group at the C-3 position of glycals, resulting in the formation of stereoselective 2,3-unsaturated glycosides at 0 °C. The catalytic amount of SnCl4 (0.1 equiv.) was successfully used to promote this transformation on 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal and 3,4-di-O-acetyl-D-arabinal using variou...
Source: Carbohydrate Research - November 28, 2023 Category: Genetics & Stem Cells Authors: Yogesh Yadav Rajdeep Tyagi Kanchan Yadav Ghanshyam Tiwari Ram Sagar Source Type: research

Expedient synthesis of l-heptose derived septacidin building blocks from l-glucose
Carbohydr Res. 2023 Nov 20;534:108985. doi: 10.1016/j.carres.2023.108985. Online ahead of print.ABSTRACTBacterial natural products containing heptosides such as septacidin represent interesting scaffolds for the development of drugs to combat antimicrobial resistance. However, very few synthetic strategies have been reported to grant access to these derivatives. Here, we have devised a synthetic pathway to l-glycero-l-glucoheptoside, a key building block en route to septacidin, directly from l-glucose. Importantly, we show that carbon homologation at C6, encompassing oxidation of the C6-OH followed by methylenation, is sig...
Source: Carbohydrate Research - November 28, 2023 Category: Genetics & Stem Cells Authors: Debashis Dhara Laurence A Mulard Marcel Hollenstein Source Type: research

Reinvestigation of SnCl < sub > 4 < /sub > catalyzed efficient synthesis of 2,3-unsaturated glycopyranosides
Carbohydr Res. 2023 Nov 23;534:108989. doi: 10.1016/j.carres.2023.108989. Online ahead of print.ABSTRACTThe Ferrier rearrangement is a powerful tool to prepare 2,3-unsaturated glycopyranosides. We have reinvestigated SnCl4 catalyzed Ferrier rearrangements through direct allylic substitution of the hydroxyl group at the C-3 position of glycals, resulting in the formation of stereoselective 2,3-unsaturated glycosides at 0 °C. The catalytic amount of SnCl4 (0.1 equiv.) was successfully used to promote this transformation on 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal and 3,4-di-O-acetyl-D-arabinal using variou...
Source: Carbohydrate Research - November 28, 2023 Category: Genetics & Stem Cells Authors: Yogesh Yadav Rajdeep Tyagi Kanchan Yadav Ghanshyam Tiwari Ram Sagar Source Type: research

An environmentally benign protocol for the synthesis of sugar 1,2-orthoesters in poly(ethylene glycol) dimethyl ether (DMPE)
Carbohydr Res. 2023 Jul 20;534:108902. doi: 10.1016/j.carres.2023.108902. Online ahead of print.ABSTRACTAn environmentally benign procedure has been developed for the synthesis of sugar orthoesters using anhydrous sodium acetate in poly (ethylene glycol)dimethyl ether (DMPE). Various sugar orthoesers were prepared without using volatile organic solvent and quaternary ammonium salt. The sugar orthoesters were obtained in good to excellent yields.PMID:38006705 | DOI:10.1016/j.carres.2023.108902 (Source: Carbohydrate Research)
Source: Carbohydrate Research - November 25, 2023 Category: Genetics & Stem Cells Authors: Jian Yang Shanqiao Wei Jinzhong Zhao Wei Zeng Huawu Shao Xiaofeng Ma Source Type: research