35920-83-3Relevant 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.
Study of Uridine 5′-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications
Lin, Geng-Min,Sun, He G.,Liu, Hung-Wen
, p. 3438 - 3441 (2016/07/26)
Uridine 5′-diphosphate-5-fluorogalactopyranose (UDP-5F-Galp, 7) was synthesized, and its effect on UDP-Galp mutase (UGM) was investigated. UGM facilitated the hydrolysis of 7 to yield UDP and 5-oxogalactose (24), but no 11 was detected. 19F NMR and trapping experiments demonstrated that the reaction involves the initial formation of a substrate-cofactor adduct followed by decomposition of the resulting C5 gem-fluorohydrin to generate a 5-oxo intermediate (10). The results support the current mechanistic proposal for UGM and suggest new directions for designing mechanism-based inhibitors.
Highly stereoselective synthesis of primary, secondary, and tertiary α-S-sialosides under lewis acidic conditions
Noel, Amandine,Delpech, Bernard,Crich, David
supporting information; experimental part, p. 4138 - 4141 (2012/10/07)
N-Acetyl 4-O,5-N-oxazolidinone protected sialyl phosphates of either anomeric configuration are excellent donors for the formation of α-S-sialosides at -78 °C in dichloromethane with primary, secondary, and tertiary thiols including galactose 3-, 4-, and
