Abstract
A sulphated form of sialyl-Lewisx, NeuAcα2-3Galβ1-4(Fucα1-3)GlcNAc6OSO3β1-3Gal, was synthesized enzymatically from a precursor disaccharide, GlcNAc6OSO3β1-3Gal, using sequential steps involving β1,4-galactosyltransferase, α2,3-trans-sialidase and recombinant α1,3-fucosyltransferase, respectively. Successful enzymatic fucosylation at the 3 position of the GlcNAc6OSO3 residue demonstrated that fucosyltransferases are capable of generating, in situ, sulphated sialyl Lewisx structures containing sulphate at the 6 position of GlcNAc. The sulphated sialyl-Lewisx pentasaccharide produced by this procedure inhibited binding of a soluble form of L-selectin to 35SO4-labelled peripheral addressin with an IC50 of 0.8 mM, whereas sialyl-Lewisx tetrasaccharide was a weaker inhibitor, displaying an IC50 of 3.2 mM. Hemmerich and Rosen (Biochemistry, 33, 4820-4829, 1994) recently reported the presence of Galβ1-4GlcNAcO6SO3 structures on murine peripheral addressin Sgp50, in addition to sialyl Lewisx structures sulphated at the 6-O-galactose position. Based on our data, we suggest that sialyl Lewisx sulphated at the 6-O-GlcNAc position may also exist on receptors and function as a ligand for L-selectin.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 929-932 |
| Number of pages | 4 |
| Journal | Glycobiology |
| Volume | 4 |
| Issue number | 6 |
| DOIs | |
| State | Published - Dec 1994 |
| Externally published | Yes |
Fingerprint
Keywords
- Homing receptor
- L-selectin
- Lymphocyte
- Peripheral addressin
- Sulphated sialyl-Lewisx
ASJC Scopus subject areas
- Statistics, Probability and Uncertainty
- Applied Mathematics
- Public Health, Environmental and Occupational Health
- Neuropsychology and Physiological Psychology
- Hematology
- Biochemistry
Cite this
Enzymatic synthesis of a 6'-sulphated sialyl-lewis which is an inhibitor of L-selectin binding to peripheral addressin. / Scudder, Peter R.; Shailubhai, Kunwar; Duffin, Kevin L.; Streeter, Philip; Jacob, Gary S.
In: Glycobiology, Vol. 4, No. 6, 12.1994, p. 929-932.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enzymatic synthesis of a 6'-sulphated sialyl-lewis which is an inhibitor of L-selectin binding to peripheral addressin
AU - Scudder, Peter R.
AU - Shailubhai, Kunwar
AU - Duffin, Kevin L.
AU - Streeter, Philip
AU - Jacob, Gary S.
PY - 1994/12
Y1 - 1994/12
N2 - A sulphated form of sialyl-Lewisx, NeuAcα2-3Galβ1-4(Fucα1-3)GlcNAc6OSO3β1-3Gal, was synthesized enzymatically from a precursor disaccharide, GlcNAc6OSO3β1-3Gal, using sequential steps involving β1,4-galactosyltransferase, α2,3-trans-sialidase and recombinant α1,3-fucosyltransferase, respectively. Successful enzymatic fucosylation at the 3 position of the GlcNAc6OSO3 residue demonstrated that fucosyltransferases are capable of generating, in situ, sulphated sialyl Lewisx structures containing sulphate at the 6 position of GlcNAc. The sulphated sialyl-Lewisx pentasaccharide produced by this procedure inhibited binding of a soluble form of L-selectin to 35SO4-labelled peripheral addressin with an IC50 of 0.8 mM, whereas sialyl-Lewisx tetrasaccharide was a weaker inhibitor, displaying an IC50 of 3.2 mM. Hemmerich and Rosen (Biochemistry, 33, 4820-4829, 1994) recently reported the presence of Galβ1-4GlcNAcO6SO3 structures on murine peripheral addressin Sgp50, in addition to sialyl Lewisx structures sulphated at the 6-O-galactose position. Based on our data, we suggest that sialyl Lewisx sulphated at the 6-O-GlcNAc position may also exist on receptors and function as a ligand for L-selectin.
AB - A sulphated form of sialyl-Lewisx, NeuAcα2-3Galβ1-4(Fucα1-3)GlcNAc6OSO3β1-3Gal, was synthesized enzymatically from a precursor disaccharide, GlcNAc6OSO3β1-3Gal, using sequential steps involving β1,4-galactosyltransferase, α2,3-trans-sialidase and recombinant α1,3-fucosyltransferase, respectively. Successful enzymatic fucosylation at the 3 position of the GlcNAc6OSO3 residue demonstrated that fucosyltransferases are capable of generating, in situ, sulphated sialyl Lewisx structures containing sulphate at the 6 position of GlcNAc. The sulphated sialyl-Lewisx pentasaccharide produced by this procedure inhibited binding of a soluble form of L-selectin to 35SO4-labelled peripheral addressin with an IC50 of 0.8 mM, whereas sialyl-Lewisx tetrasaccharide was a weaker inhibitor, displaying an IC50 of 3.2 mM. Hemmerich and Rosen (Biochemistry, 33, 4820-4829, 1994) recently reported the presence of Galβ1-4GlcNAcO6SO3 structures on murine peripheral addressin Sgp50, in addition to sialyl Lewisx structures sulphated at the 6-O-galactose position. Based on our data, we suggest that sialyl Lewisx sulphated at the 6-O-GlcNAc position may also exist on receptors and function as a ligand for L-selectin.
KW - Homing receptor
KW - L-selectin
KW - Lymphocyte
KW - Peripheral addressin
KW - Sulphated sialyl-Lewisx
UR - http://www.scopus.com/inward/record.url?scp=0028597483&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0028597483&partnerID=8YFLogxK
U2 - 10.1093/glycob/4.6.929
DO - 10.1093/glycob/4.6.929
M3 - Article
VL - 4
SP - 929
EP - 932
JO - Glycobiology
JF - Glycobiology
SN - 0959-6658
IS - 6
ER -