15753-48-7Relevant articles and documents
A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx
Conti, Gabriele,Cramer, Jonathan,Ernst, Beat,Girardi, Benedetta,Jiang, Xiaohua,Kokot, Maja,Kroezen, Blijke S.,Luisoni, Enrico,Müller, Jennifer,Rabbani, Said,Ricklin, Daniel,Schwardt, Oliver
supporting information, p. 1706 - 1719 (2020/09/02)
Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.
Regiochemical Control of the Ring-Opening of 1,2-Epoxides by Means of Chelating Processes. 2. Synthesis and Reactions of the cis- and trans-Oxides of 4-cyclohexene, 3-Cyclohexenemethanol, and Methyl 3-Cyclohexenecarboxylate
Chini, Marco,Crotti, Paolo,Flippin, Lee A.,Macchia, Franco,Pineschi, Mauro
, p. 1405 - 1412 (2007/10/02)
The synthesis of the diastereoisomeric epoxides cis-1b-d and trans-2b-d and the products of their ring-opening by various nucleophiles are described.The results of the ring-openings of the trans-epoxides 2b-d can be rationalized by combining stereoelectro
