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Role of the galactosyl moiety of collagen glycopeptides for T-cell stimulation in a model for rheumatoid arthritis

Holm, B ; Baquer, SM ; Holm, L ; Holmdahl, Rikard LU and Kihlberg, J (2003) In Bioorganic & Medicinal Chemistry 11(18). p.3981-3987
Abstract
Two protected derivatives of beta-D-galactopyranosyl-5-hydroxy-L-lysine, in which HO-4 of galactose has been O-methylated or replaced by fluorine, have been prepared. The building blocks were incorporated at position 264 of the peptide fragment CII259-273 from type II collagen by solid-phase synthesis. The ability of these two glycopeptides, and two CII259-273 glycopeptides in which HO-4 of galactose was either unmodified or deoxygenated, to elicit responses from T-cell hybridomas obtained in a mouse model for rheumatoid arthritis was then determined. The hybridomas were all highly sensitive towards modifications at C-4 of the beta-D-galactosyl residue of CII259-273, highlighting the role of HO-4 as an important contact point for the... (More)
Two protected derivatives of beta-D-galactopyranosyl-5-hydroxy-L-lysine, in which HO-4 of galactose has been O-methylated or replaced by fluorine, have been prepared. The building blocks were incorporated at position 264 of the peptide fragment CII259-273 from type II collagen by solid-phase synthesis. The ability of these two glycopeptides, and two CII259-273 glycopeptides in which HO-4 of galactose was either unmodified or deoxygenated, to elicit responses from T-cell hybridomas obtained in a mouse model for rheumatoid arthritis was then determined. The hybridomas were all highly sensitive towards modifications at C-4 of the beta-D-galactosyl residue of CII259-273, highlighting the role of HO-4 as an important contact point for the T-cell receptor. Most likely, this glycopeptide hydroxyl group is involved in hydrogen bonding with the T-cell receptor. (C) 2003 Elsevier Ltd. All rights reserved. (Less)
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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Bioorganic & Medicinal Chemistry
volume
11
issue
18
pages
3981 - 3987
publisher
Elsevier
external identifiers
  • wos:000185037900015
  • pmid:12927859
  • scopus:0043092066
ISSN
0968-0896
DOI
10.1016/S0968-0896(03)00407-3
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Medical Inflammation Research (013212019)
id
b7ef5824-7336-4096-8cd1-3a712c4eabcb (old id 302328)
date added to LUP
2016-04-01 12:30:48
date last changed
2022-02-03 23:12:47
@article{b7ef5824-7336-4096-8cd1-3a712c4eabcb,
  abstract     = {{Two protected derivatives of beta-D-galactopyranosyl-5-hydroxy-L-lysine, in which HO-4 of galactose has been O-methylated or replaced by fluorine, have been prepared. The building blocks were incorporated at position 264 of the peptide fragment CII259-273 from type II collagen by solid-phase synthesis. The ability of these two glycopeptides, and two CII259-273 glycopeptides in which HO-4 of galactose was either unmodified or deoxygenated, to elicit responses from T-cell hybridomas obtained in a mouse model for rheumatoid arthritis was then determined. The hybridomas were all highly sensitive towards modifications at C-4 of the beta-D-galactosyl residue of CII259-273, highlighting the role of HO-4 as an important contact point for the T-cell receptor. Most likely, this glycopeptide hydroxyl group is involved in hydrogen bonding with the T-cell receptor. (C) 2003 Elsevier Ltd. All rights reserved.}},
  author       = {{Holm, B and Baquer, SM and Holm, L and Holmdahl, Rikard and Kihlberg, J}},
  issn         = {{0968-0896}},
  language     = {{eng}},
  number       = {{18}},
  pages        = {{3981--3987}},
  publisher    = {{Elsevier}},
  series       = {{Bioorganic & Medicinal Chemistry}},
  title        = {{Role of the galactosyl moiety of collagen glycopeptides for T-cell stimulation in a model for rheumatoid arthritis}},
  url          = {{http://dx.doi.org/10.1016/S0968-0896(03)00407-3}},
  doi          = {{10.1016/S0968-0896(03)00407-3}},
  volume       = {{11}},
  year         = {{2003}},
}