55529-69-6Relevant articles and documents
Cholesteryl glucosides signal through the carbohydrate recognition domain of the macrophage inducible C-type lectin (mincle)
Timmer, Mattie S. M.,Teunissen, Thomas J.,Kodar, Kristel,Foster, Amy J.,Yamasaki, Sho,Stocker, Bridget L.
supporting information, p. 2198 - 2202 (2021/03/24)
Cholesteryl α-d-glucosides (αGCs) are unique metabolic products of the cancer-causing human pathogenHelicobacter pylori.Viasignalling through the Macrophage inducible C-type lectin (Mincle) and the induction of a pro-inflammatory response, they are thought to play a role in the development of gastric atrophy. Herein, we prepared the first library of steryld-glucosides and determined that they preferentially signal through the carbohydrate recognition domain of human Mincle, rather than the amino acid consensus motif. Lipidated steryld-glucosides exhibited enhanced Mincle agonist activity, with C18 cholesteryl 6-O-acyl-α-d-glucoside (2c) being the most potent activator of human monocytes. Despite exhibiting strong Mincle signalling, sito- (5b) and stigmasterol glycosides (6b) led to a poor inflammatory response in primary cells, suggesting that Mincle is a potential therapeutic target for preventingH. pylori-mediated inflammation and cancer.
Selective Acetylation of Non-anomeric Groups of per- O-Trimethylsilylated Sugars
Weldu, Welday Desta,Wang, Cheng-Chung
, p. 5336 - 5344 (2021/04/02)
Selective modification of the hydroxyl groups of sugars has been a long-standing challenge due to their proximate relative reactivity. Herein, we report a TMSOTf-catalyzed selective acetylation of the non-anomeric hydroxyl groups of several per-O-TMS-protected sugar substrates while leaving their anomeric group unaffected. In addition to standing versatile by itself, the anomeric O-TMS group left intact can be functionalized to afford key sugar precursors such as imidate donors, which could otherwise be synthesized via a stepwise anomeric deprotection-functionalization procedure.
Development of a Novel Method for Trimethylsilylation of Saccharides?
Chen, Jyun-Siao,Ke, Yi-Fan,Lin, Heng-Yan,Lin, Wesley,Yen, Wei-Chung,Wu, Hsin-Ru,Luo, Shun-Yuan
, p. 2000 - 2006 (2021/02/01)
The trimethylsilyl (TMS) group is widely used in carbo?hydrate synthesis, although this protecting group is unstable and its post-synthetic purification challenging. The successful trimethylsilyl?ation of carbohydrates mediated by recyclable and efficient