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Details van artikel 88 van 118 gevonden artikelen
| Titel: |
Synthesis of Immunosuppressive Neoglycoproteins: Bovine Serum Albumin Coupled with 8-(Hydrazino-Carbonyl)Octyl 4- Or 6-O-α-D-Mannopyranosyl-α-D-Mannopyranoside |
| Auteur: |
Wada, Kaoru Chiba, Taku Takei, Yutaka Ishihara, Hideko Hayashi, Hidetoshi Onozaki, Kikuo |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 13 (1994) nr. 7 pagina's 941-965 |
| Jaar: |
1994-10-01 |
| Inhoud: |
Recombinant cytokines generated by bacteria, especially E. coli, are nonglycosylated. To investigate the effects of carbohydrates on their activities, we attempted to develop new cytokines by introduction of carbohydrates. As a model we synthesized neoglycoproteins in which potential immunoregulatory carbohydrates were coupled to bovine serum albumin(BSA). Mannose dimers with C9 spacer, Manα1-6Man, which is reported to be immunosuppressive, and a reference substance Manα1-4Man were synthesized as follows. Benzylidenation of 8-(methoxycarbonyl)octyl α-D-mannopyranoside (10), followed by acetylation and cleavage of the benzylidene acetal, gave a glycosyl acceptor (13) with a free hydroxyl group in the C-4 position. Glycosylation of 13 with acetobromomannose (8), followed by debenzylation, deacetylation, and hydrazidation, gave 8-(hydrazinocarbonyl)octyl 4-O-α-D-mannopyranosyl-α-D-mannopyranoside (1). Total yield of 1 from 10 was 25.1%. Tritylation of 10, followed by acetylation and detritylation, gave a glycosyl acceptor (18) with a free hydroxyl group in the C-6 position. Analogous condensation of 18 with 8, followed by deacetylation and hydrazidation, gave 8-(hydrazinocarbonyl)octyl 6-O-α-D-mannopyranosyl-α-D-mannopyranoside (2). Total yield of 2 from 10 was 22.9%. These mannose dimers were coupled to BSA by the acyl azide method. Using the antibodies against the mannose dimers, an enzyme linked immunosorbent assay (ELISA) was established to measure the small amount of mannose dimers coupled to proteins. These two neoglycoproteins appeared to inhibit the antigen-specific human T cell proliferation over 100 fold more efficiently than free mannose dimers. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 88 van 118 gevonden artikelen
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