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J Biol Chem, Vol. 274, Issue 16, 10697-10705, April 16, 1999
From the Laboratory of Cancer Biology and Molecular Immunology,
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
A fluorescein-labeled synthetic peptide,
PTTTPITTTTK, was converted into O-glycosylated
glycopeptides with various numbers of attached
N-acetyl-D-galactosamines (GalNAcs) by in
vitro glycosylation with UDP-GalNAc and a microsomal fraction
of LS174T human colon carcinoma cells. Glycopeptides with 1, 3, 5, and
6 GalNAc residues (G1, G3, G5, and G6) were obtained, and their sizes
were confirmed by matrix-assisted laser desorption ionization
time-of-flight mass spectrometry. Their sequences were determined by a
peptide sequencer to be PTTTGalNAcPITTTTK for G1,
PTGalNAcTTPITGalNAcTGalNAcTTK for G3,
PTTGalNAcTGalNAcPITGalNAcTGalNAcTGalNAcTK
for G5, and PTGalNAcTGalNAcTGalNAcPITGalNAcTGalNAcTGalNAcTK
for G6. A calcium-type human macrophage lectin (HML) was prepared in a
recombinant form, and its interaction with these glycopeptides was
investigated by surface plasmon resonance (SPR) spectroscopy and
fluorescence polarization. The affinity of recombinant HML (rHML) for
immobilized glycopeptides increased, as revealed by SPR, in
parallel with the number of GalNAc. The highest affinity was obtained
when the G6-peptide was immobilized at high density. Fluorescence
polarization equilibrium-binding assays also revealed that the
affinity of rHML for soluble gly-copeptides increased, depending on the
number of attached GalNAcs. Carbohydrate recognition domain
(CRD) fragments of HML were prepared, and their affinity for these four
glycopeptides was also determined, this affinity was
apparently lower than that of rHML. Affinity constants of rHML for the
G3- and G5-peptides were 11- and 38-fold higher, respectively, than for
the G1-peptide, whereas those of CRD fragments were only 2- and 6-fold
higher, respectively. A chemical cross-linking study revealed that rHML but not recombinant CRD forms trimers in an aqueous solution. Thus, preferential binding of densely glycosylated
O-linked glycopeptides should be due to the trimer
formation of rHML.
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