Molecular recognition. II. The binding of the Lewis b and Y human blood group determinants by the lectin IV of Griffoniasimplicifolia
Using a radioimmunoassay to measure the relative potencies as inhibitors of a wide number of chemically modified structures related to the Lewis b human blood group determinant, it was found that derivatives of the Lewis b (α L Fuc(1→2)β D Gal(1→3)[α L Fuc(1→4)]β D GlcNAc) and the Y (α L Fuc(1→2)P D...
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Veröffentlicht in: | Canadian journal of chemistry 1985-10, Vol.63 (10), p.2644-2652 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng ; jpn |
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Zusammenfassung: | Using a radioimmunoassay to measure the relative potencies as inhibitors of a wide number of chemically modified structures related to the Lewis b human blood group determinant, it was found that derivatives of the Lewis b (α
L
Fuc(1→2)β
D
Gal(1→3)[α
L
Fuc(1→4)]β
D
GlcNAc) and the Y (α
L
Fuc(1→2)P
D
Gal(1→4)[α
L
Fuc(1→3)]β
D
GlcNAc) determinants are complexed by the lectin IV of Griffoniasimplicifolia through the recognition of a topographical feature that is common to both the tetrasaccharides. This surface provides a nonpolar region formed by the two methyl groups of the fucose units and extends along the C-1O-5C-5 side of the α
L
Fuc(1→2) unit and terminates at one end by a polar grouping which is formed by OH-3 and OH-4 of the β
D
Gal unit and OH-4 of the α
L
Fuc(1→4) unit. Association constants were determined from changes in ultraviolet absorption that occur as the result of complex formation. For the reaction of the Lewis b-OCH
3
tetrasaccharide, the thermodynamic parameters were found to be ΔH = −13 kcal/mol and ΔS = −22 cal/mol/K. The inhibition data for the relevant monodeoxy derivatives indicated that OH-2 and OH-3 of both of the α
L
Fuc units are not directly involved in the binding reaction. The basis for drawing these conclusions was strengthened by finding that the reaction of the simple Lewis b analog, methoxymethyl (1→2)β
D
Gal(1→3)[α
L
Fuc(1→4)]β
D
GlcNAcOCH
3
displayed very similar thermodynamic values; namely, ΔH = −14 kcal/mol and ΔS = −26 cal/mol/K, to those mentioned above for the Le
b
-OCH
3
tetrasaccharide. The OH-4 of the α
L
Fuc(1→2) unit may be bound in an intramolecularly hydrogen bonded form. |
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ISSN: | 0008-4042 1480-3291 |
DOI: | 10.1139/v85-439 |