IUPAC 名称
(2S,4S,5R,6R)-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-3-acetamido-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
描述
Sialyl Lewisa pentasaccharide is a human E-selectin (endothelial adhesion molecule) ligand. The cell adhesion molecule E-selectin, which is expressed on cytokine-stimulated endothelial cells, binds to neutrophils, monocytes, and a subpopulation of memory T-cells. This protein has an established role at the initial stepins the recruitment of leukocytes to sites of inflammation, and there is also much interest in the part that it plays in the hematogenous spread of cancer cells. Interference with selectin binding results in inhibition of the later steps that promote leukocyte extravasation. There is therefore much interest in defining the ligands that support adhesion, as a lead to design of adhesion inhibitors that may serve as drugs for the treatment of disorders of inflammation and for minimizing risk of metastasis during surgical resections of tumors.
As predicted from the presence of a lectin-like module at the amino-terminal endof the extracellular domain, E-selectin is a carbohydrate-binding protein. The established ligands for E-selectin include a family of blood group-related fucooligosaccharides that occur as differentiation antigens of granulocytes and monocytes (Lex and 3'-sialyl-Lex) and of epithelial tumors (Lea and 3'-sialyl-Lea). Adhesion to the sialyl antigens is substantially greater than to the asialo analogues (PMID:7507478)
[HMDB]
InChI标识符
InChI=1S/C43H72N2O33/c1-11-23(58)28(63)29(64)39(69-11)74-33-20(10-51)72-38(76-36-26(61)18(8-49)70-40(30(36)65)73-32(17(57)7-48)24(59)15(55)5-46)22(45-13(3)53)35(33)75-41-31(66)37(27(62)19(9-50)71-41)78-43(42(67)68)4-14(54)21(44-12(2)52)34(77-43)25(60)16(56)6-47/h5,11,14-41,47-51,54-66H,4,6-10H2,1-3H3,(H,44,52)(H,45,53)(H,67,68)/t11-,14-,15-,16+,17+,18+,19+,20+,21+,22+,23+,24+,25+,26-,27-,28+,29-,30+,31+,32+,33+,34+,35?,36-,37?,38-,39-,40-,41-,43-/m0/s1