Sialyl-Lewis X - Misplaced Pages

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Sialyl-Lewis X
Identifiers

CAS Number	98603-84-0
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL375586
ChemSpider	559072
MeSH	sialyl+Lewis+X
PubChem CID	643990
CompTox Dashboard (EPA)	DTXSID60913167
InChI InChI=1S/C31H52N2O23/c1-9-18(43)21(46)22(47)28(51-9)53-24(12(5-34)32-10(2)38)25(15(42)7-36)54-29-23(48)27(20(45)16(8-37)52-29)56-31(30(49)50)4-13(40)17(33-11(3)39)26(55-31)19(44)14(41)6-35/h5,9,12-29,35-37,40-48H,4,6-8H2,1-3H3,(H,32,38)(H,33,39)(H,49,50)/t9-,12-,13-,14+,15+,16+,17+,18+,19+,20-,21+,22-,23+,24+,25+,26+,27-,28-,29-,31-/m0/s1Key: LAQPKDLYOBZWBT-NYLDSJSYSA-N InChI=1/C31H52N2O23/c1-9-18(43)21(46)22(47)28(51-9)53-24(12(5-34)32-10(2)38)25(15(42)7-36)54-29-23(48)27(20(45)16(8-37)52-29)56-31(30(49)50)4-13(40)17(33-11(3)39)26(55-31)19(44)14(41)6-35/h5,9,12-29,35-37,40-48H,4,6-8H2,1-3H3,(H,32,38)(H,33,39)(H,49,50)/t9-,12-,13-,14+,15+,16+,17+,18+,19+,20-,21+,22-,23+,24+,25+,26+,27-,28-,29-,31-/m0/s1Key: LAQPKDLYOBZWBT-NYLDSJSYBC
SMILES O=C(N1(O)C(O1(O)(O)CO)(O2(O)(O(CO)2O)O((O3O((O)(O)3O)C)(C=O)NC(=O)C)(O)CO)C(=O)O)C
Properties
Chemical formula	C₃₁H₅₂N₂O₂₃
Molar mass	820.744 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Sialyl Lewis, also known as sialyl Le and SLe, is a tetrasaccharide carbohydrate that is usually attached to O-glycans on the surface of cells. It is known to play a vital role in cell-to-cell recognition processes. Sialyl Lewis is one of the most important blood group antigens and is displayed on the terminus of glycolipids that are present on the cell surface. The Sialyl Lewis determinant, E-selectin ligand carbohydrate structure, is constitutively expressed on granulocytes and monocytes and mediates inflammatory extravasation of these cells. Resting T and B lymphocytes lack its expression and are induced to strongly express sialyl Lewis upon activation. The Sialyl Lewis determinant is expressed preferentially on activated Th1 cells but not on Th2 cells.

Clinical significance

Defective synthesis of the sialyl Lewis antigen results in immunodeficiency (leukocyte adhesion deficiency type 2). Defective synthesis can be caused by the loss of fucosyltransferase, impairing the glycosylation of the glycosphingolipid.

Sources

Stephen J Isles, Molecule of the Month: Sialyl Lewis X
Chen G, Osada H, Santamaria-Babi L, Kannagi R (2006). "Interaction of GATA-3/T-bet transcription factors regulates expression of sialyl Lewis X homing receptors on Th1/Th2 lymphocytes". Proc Natl Acad Sci USA. 103 (45): 16894–9. doi:10.1073/pnas.0607926103. PMC 1629005. PMID 17075044.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Clinical significance

Sources

See also