1541178-86-2Relevant academic research and scientific papers
Cholesteryl 6-: O-acyl-α-glucosides from diverse Helicobacter spp. signal through the C-type lectin receptor Mincle
Ito, Emi,Smith, Dylan G. M.,Williams, Spencer J.,Yamasaki, Sho
, p. 7907 - 7915 (2020/11/02)
Helicobacter spp. are Gram-negative bacteria that cause a spectrum of disease in the gut, biliary tree and liver. Many Helicobacter spp. produce a range of cholesteryl α-glucosides that have the potential to act as pathogen associated molecular patterns. We report a highly stereoselective α-glucosylation of cholesterol using 3,4,6-tri-O-acetyl-2-O-benzyl-d-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate, which allowed the synthesis of cholesteryl α-glucoside (αCG) and representative Helicobacter spp. cholesteryl 6-O-acyl-α-glucosides (αCAGs; acyl = C12:0, 14:0, C16:0, C18:0, C18:1). All αCAGs, irrespective of the nature of their acyl chain composition, strongly agonised signalling through the C-type lectin receptor Mincle from human and mouse to similar degrees. By contrast, αCG only weakly signalled through human Mincle, and did not signal through mouse Mincle. These results provide a molecular basis for understanding of the immunobiology of non-pylori Helicobacter infections in humans and other animals. This journal is
Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? the role of conformational mobility and the protecting group at O-6
Komarova, Bozhena S.,Orekhova, Maria V.,Tsvetkov, Yury E.,Nifantiev, Nikolay E.
, p. 70 - 76 (2014/04/03)
The stereodirecting effect of a 3-O-acetyl protecting group, which is potentially capable of the remote anchimeric participation, and other protecting groups in 2-O-benzyl glucosyl donors with flexible and rigid conformations has been investigated. To this aim, an array of N-phenyltrifluoroacetimidoyl and sulfoxide donors bearing either 3-O-acetyl or 3-O-benzyl groups in combination with 4,6-di-O-benzyl, 6-O-acyl-4-O-benzyl, or 4,6-O-benzylidene protecting groups was prepared. The conformationally flexible 3-O-acetylated glucosyl donor protected at other positions with O-benzyl groups demonstrated very low or no α-stereoselectivity upon glycosylation of primary or secondary acceptors. On the contrary, 3,6-di-O-acylated glucosyl donors proved to be highly α-stereoselective as well as the donor having a single potentially participating acetyl group at O-6. The 3,6-di-O-acylated donor was shown to be the best α-glucosylating block for the primary acceptor, whereas the best α-selectivity of glycosylation of the secondary acceptor was achieved with the 6-O-acylated donor. Glycosylation of the secondary acceptor with the conformationally constrained 3-O-acetyl-4,6-O-benzylidene-protected donor displayed under standard conditions (-35 C) even lower α-selectivity as compared to the 3-O-benzyl analogue. However, increasing the reaction temperature essentially raised the α-stereoselectivities of glycosylation with both 3-O-acetyl and 3-O-benzyl donors and made them almost equal. The stereodirecting effects of protecting groups observed for N- phenyltrifluoroacetimidoyl donors were also generally proven for sulfoxide donors.2013 Elsevier Ltd. All rights reserved.
