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J Biol Chem, Vol. 274, Issue 35, 24838-24848, August 27, 1999
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From the Departments of P-selectin glycoprotein ligand-1 (PSGL-1) is a
dimeric membrane mucin on leukocytes that binds selectins. The
molecular features of PSGL-1 that determine this high affinity binding
are unclear. Here we demonstrate the in vitro synthesis of
a novel glycosulfopeptide (GSP-6) modeled after the extreme N terminus
of PSGL-1, which has been predicted to be important for P-selectin
binding. GSP-6 contains three tyrosine sulfate (TyrSO3)
residues and a monosialylated, core 2-based O-glycan with a
sialyl Lewis x (C2-O-sLex) motif at a specific
Thr residue. GSP-6 binds tightly to immobilized P-selectin, whereas
glycopeptides lacking either TyrSO3 or
C2-O-sLex do not detectably bind. Remarkably,
an isomeric glycosulfopeptide to GSP-6, termed GSP-6', which contains
sLex on an extended core 1-based O-glycan, does
not bind immobilized P-selectin. Equilibrium gel filtration analysis
revealed that GSP-6 binds to soluble P-selectin with a
Kd of ~350 nM. GSP-6 (<5
µM) substantially inhibits neutrophil adhesion to
P-selectin in vitro, whereas free sLex (5 mM) only slightly inhibits adhesion. In contrast to the
inherent heterogeneity of post-translational modifications of
recombinant proteins, glycosulfopeptides permit the placement of
sulfate groups and glycans of precise structure at defined positions on
a polypeptide. This approach should expedite the probing of
structure-function relationships in sulfated and glycosylated proteins,
and may facilitate development of novel drugs to treat inflammatory
diseases involving P-selectin-mediated leukocyte adhesion.
Biochemistry and Molecular
Biology and ¶ Medicine, the W. K. Warren Medical
Research Institute, Department of Medical
Chemistry, Vrije Universiteit, Amsterdam 1081, The Netherlands
Copyright © 1999 by The American Society for Biochemistry and Molecular Biology, Inc.
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