1374561-92-8Relevant academic research and scientific papers
Trisaccharide Sulfate and Its Sulfonamide as an Effective Substrate and Inhibitor of Human Endo- O-sulfatase-1
Cheng, Ting-Jen Rachel,Chiu, Li-Ting,Fan, Chiao-Yuan,Hung, Shang-Cheng,Lin, Wei-Chen,Sabbavarapu, Narayana Murthy,Wong, Chi-Huey,Wu, Chih-Chung
, p. 5282 - 5292 (2020/04/08)
Human endo-O-sulfatases (Sulf-1 and Sulf-2) are extracellular heparan sulfate proteoglycan (HSPG)-specific 6-O-endosulfatases, which regulate a multitude of cell-signaling events through heparan sulfate (HS)-protein interactions and are associated with th
α-glycosylation by d -glucosamine-derived donors: Synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin
Zulueta, Medel Manuel L.,Lin, Shu-Yi,Lin, Ya-Ting,Huang, Ching-Jui,Wang, Chun-Chih,Ku, Chiao-Chu,Shi, Zhonghao,Chyan, Chia-Lin,Irene, Deli,Lim, Liang-Hin,Tsai, Tsung-I,Hu, Yu-Peng,Arco, Susan D.,Wong, Chi-Huey,Hung, Shang-Cheng
supporting information; experimental part, p. 8988 - 8995 (2012/07/02)
Numerous biomolecules possess α-d-glucosamine as structural component. However, chemical glycosylations aimed at this backbone are usually not easily attained without generating the unwanted β-isomer. We report herein a versatile approach in affording full α-stereoselectivity built upon a carefully selected set of orthogonal protecting groups on a d-glucosaminyl donor. The excellent stereoselectivity provided by the protecting group combination was found independent of leaving groups and activators. With the trichloroacetimidate as the optimum donor leaving group, core skeletons of glycosylphosphatidyl inositol anchors, heparosan, heparan sulfate, and heparin were efficiently assembled. The orthogonal protecting groups were successfully manipulated to further carry out the total syntheses of heparosan tri- and pentasaccharides and heparin di-, tetra-, hexa-, and octasaccharide analogues. Using the heparin analogues, heparin-binding hemagglutinin, a virulence factor of Mycobacterium tuberculosis, was found to bind at least six sugar units with the interaction notably being entropically driven.
