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'''Sialyl Lewis<sup>X</sup>''', also known as ''sialyl Le<sup>X</sup>'' and ''SLe<sup>X</sup>'', 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. It is also the means in which an egg attracts sperm - first to stick to it, then bond with it and eventually form a fetus. The discovery of the essential role that this tetrasaccharide plays in the fertilization process was made in August of 2011.
'''Sialyl Lewis<sup>X</sup>''', also known as ''sialyl Le<sup>X</sup>'' and ''SLe<sup>X</sup>'', 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. It is also the means in which an egg attracts sperm - first to stick to it, then bond with it and eventually form a fetus. The discovery of the essential role that this tetrasaccharide plays in the fertilization process was made in August of 2011.<ref>{{cite journal|last=Pang|first=Poh-Choo|coauthors=Chiu, Lee, Chang, et al.|title=Human Sperm Binding Is Mediated by the Sialyl-Lewisx Oligosaccharide on the Zona Pellucida|journal=Science|date=18|year=2011|month=August|volume=333|issue=6050|pages=1761-1764|doi=10.1126/science.1207438|url=http://www.sciencemag.org/content/333/6050/1761.abstract|accessdate=23 October 2011}}</ref>


''Sialyl Lewis <sup>X</sup>'' is also 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 <sup>X</sup>'' determinant, E-[[selectin]] ligand carbohydrate structure, is constitutively expressed on [[granulocyte]]s and [[monocyte]]s and mediates inflammatory extravasation of these cells. Resting T and B [[lymphocyte]]s lack its expression and are induced to strongly express ''sialyl Lewis <sup>X</sup>'' upon activation. The ''Sialyl Lewis <sup>X</sup>'' determinant is expressed preferentially on activated Th1 cells but not on Th2 cells.
''Sialyl Lewis <sup>X</sup>'' is also 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 <sup>X</sup>'' determinant, E-[[selectin]] ligand carbohydrate structure, is constitutively expressed on [[granulocyte]]s and [[monocyte]]s and mediates inflammatory extravasation of these cells. Resting T and B [[lymphocyte]]s lack its expression and are induced to strongly express ''sialyl Lewis <sup>X</sup>'' upon activation. The ''Sialyl Lewis <sup>X</sup>'' determinant is expressed preferentially on activated Th1 cells but not on Th2 cells.
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==Sources==
==Sources==
*[http://www.chm.bris.ac.uk/motm/sla/sialyl.html Stephen J Isles, Molecule of the Month: Sialyl Lewis X]
* [http://www.chm.bris.ac.uk/motm/sla/sialyl.html Stephen J Isles, Molecule of the Month: Sialyl Lewis X]
* {{cite journal |author=Chen G, Osada H, Santamaria-Babi L, Kannagi R |title=Interaction of GATA-3/T-bet transcription factors regulates expression of sialyl Lewis X homing receptors on Th1/Th2 lymphocytes |journal=Proc Natl Acad Sci USA |volume=103 |issue=45 |pages=16894–9 |year=2006 |pmid=17075044 |doi=10.1073/pnas.0607926103 |pmc=1629005}}
* {{cite journal |author=Chen G, Osada H, Santamaria-Babi L, Kannagi R |title=Interaction of GATA-3/T-bet transcription factors regulates expression of sialyl Lewis X homing receptors on Th1/Th2 lymphocytes |journal=Proc Natl Acad Sci USA |volume=103 |issue=45 |pages=16894–9 |year=2006 |pmid=17075044 |doi=10.1073/pnas.0607926103 |pmc=1629005}}
* {{cite journal|last=Pang|first=Poh-Choo|coauthors=Chiu, Lee, Chang, et al.|title=Human Sperm Binding Is Mediated by the Sialyl-Lewisx Oligosaccharide on the Zona Pellucida|journal=Science|date=18|year=2011|month=August|volume=333|issue=6050|pages=1761-1764|doi=10.1126/science.1207438|url=http://www.sciencemag.org/content/333/6050/1761.abstract|accessdate=23 October 2011}}


== See also==
== See also==

Revision as of 02:12, 23 October 2011

Sialyl-Lewis X
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH sialyl+Lewis+X
  • 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/s1 checkY
    Key: LAQPKDLYOBZWBT-NYLDSJSYSA-N checkY
  • 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/s1
    Key: LAQPKDLYOBZWBT-NYLDSJSYBC
  • O=C(N[C@@H]1[C@@H](O)C[C@](O[C@H]1[C@H](O)[C@H](O)CO)(O[C@@H]2[C@@H](O)[C@@H](O[C@H](CO)[C@@H]2O)O[C@@H]([C@H](O[C@@H]3O[C@H]([C@@H](O)[C@@H](O)[C@@H]3O)C)[C@H](C=O)NC(=O)C)[C@H](O)CO)C(=O)O)C
Properties
C31H52N2O23
Molar mass 820.744 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Sialyl LewisX, also known as sialyl LeX and SLeX, 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. It is also the means in which an egg attracts sperm - first to stick to it, then bond with it and eventually form a fetus. The discovery of the essential role that this tetrasaccharide plays in the fertilization process was made in August of 2011.[1]

Sialyl Lewis X is also 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 X 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 X upon activation. The Sialyl Lewis X determinant is expressed preferentially on activated Th1 cells but not on Th2 cells.

Clinical significance

Defective synthesis of the sialyl Lewis X 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)
  • Pang, Poh-Choo (18). "Human Sperm Binding Is Mediated by the Sialyl-Lewisx Oligosaccharide on the Zona Pellucida". Science. 333 (6050): 1761–1764. doi:10.1126/science.1207438. Retrieved 23 October 2011. {{cite journal}}: Check date values in: |date= and |year= / |date= mismatch (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

See also


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  1. ^ Pang, Poh-Choo (18). "Human Sperm Binding Is Mediated by the Sialyl-Lewisx Oligosaccharide on the Zona Pellucida". Science. 333 (6050): 1761–1764. doi:10.1126/science.1207438. Retrieved 23 October 2011. {{cite journal}}: Check date values in: |date= and |year= / |date= mismatch (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
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