Role of the galactosyl moiety of collagen glycopeptides for T-cell stimulation in a model for rheumatoid arthritis |
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| Authors: | Holm Björn Baquer Syed M Holm Lotta Holmdahl Rikard Kihlberg Jan |
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| Institution: | 1. Organic Chemistry, Department of Chemistry, Umeå University, SE-901 87 Umeå, Sweden;2. Section of Medical Inflammation Research, Lund University, Sölvegatan 19, I11 BMC, SE-221 84 Lund, Sweden;1. Department of Chemistry, Universidade Estadual de Ponta Grossa, Av. General Carlos Cavalcanti, 4748, 84030-900 Ponta Grossa, Paraná, Brazil;2. Department of Chemistry, Instituto Federal do Paraná, Rodovia PR 323, KM 310, 87507-014 Umuarama, Paraná, Brazil;3. Department of Basic Pathology, Universidade Federal do Paraná, Av. Coronel Francisco H. dos Santos, 100, 81530-000 Curitiba, Paraná, Brazil;4. Department of Community Health, Universidade Federal do Paraná, Rua Padre Camargo, 261, 80069-240 Curitiba, Paraná, Brazil;5. Instituto de Pesquisa Pelé Pequeno Príncipe, Av. Silva Jardim, 1632, 80250-060 Curitiba, Paraná, Brazil;1. Centre for Transport Studies Dept. Civil, Environmental & Geomatic Engineering, Chadwick Building, Room 209 University College London Gower St, London WC1E 6BT, United Kingdom;2. Monash University, 553 St Kilda Rd, Melbourne, VIC 3004, Australia;3. Tamaki Building 730 - Bldg 730 Level 4, Room 438 Tamaki Campus Gate 1, 261 Morrin Rd St Johns, Auckland 1072 New Zealand;4. The Royal Children''s Hospital Melbourne, 50 Flemington Rd, Parkville, VIC 3052, Australia;1. ISTRA, Department of Chemistry, MCE Society’s Abeda Inamdar Senior College of Arts, Science and Commerce, University of Pune, Pune 411001, India;2. Department of Animal Sciences, School of Life Sciences, University of Hyderabad, Hyderabad 500046, India;3. Department of Bioinformatics and Computer Science, Dr. D. Y. Patil Biotechnology and Bioinformatics Institute, Dr. D. Y. Patil Vidyapeeth, Pune 411044, India;1. Department of Orthopedic Surgery, Unnan City Hospital, Shimane, Japan;2. Internal Medicine 1, Shimane University Faculty of Medicine, Shimane, Japan;3. Department of Musculoskeletal Traumatology, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama, Japan;4. Department of Orthopaedic Surgery, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Science, Okayama, Japan |
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| 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. |
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