37 腎炎発症糖ペプチド・ネフリトゲノシドの合成研究(ポスター発表の部)
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Nephritogenoside, isolated from the basement membrane of rats, is a nephritogenic glycopeptide whose structure 1 was determined by S. Shibata et al. in 1988. In the molecule of nephritogenoside, the trisaccharide containing three glucose moieties is linked with the peptide composed of 21 amino acids via N-glycoside bond on the asparagine residue. We planned the synthetic study of this glycopeptide in order to confirm the proposed structure and to elucidate the structure-activity relationship. In our synthetic strategy, allyloxycarbonyl group which is removable by palladium complex under neutral conditions was chosen as the final protecting group, taking account of general unstability of glycopeptide under acidic and basic conditions. Trisaccharide 4 was synthesized from heptaacetylisomaltosyl fluoride and 2,3,4-triacetylglucopyranosyl azide. The compound 4 was reduced followed by acylation with Aloc-Asp(OH)-O^tBu to give N-glycoside 5. After replacement of acetyl group with Aloe group, the coupling with the eicosapeptide (2-21) was attempted. However, N-hydroxysuccinimide active ester (7) did not react with the peptide but cyclized itself to give the succinimide derivative of 7. Therefore, we then tried a coupling of the active ester of glycosyldipeptide (1-2) (10) with nonadecapeptide (3-21). This reaction gave us a desirable protected nephritogenoside. After deprotection of all Aloc group by palladium complex, the crude product was purified by HPLC to give free nephritogenoside. In this study, we established the synthetic strategy for glycopeptide with relatively long peptide chain. The glycodipeptide was coupled with an appropriate peptide using Aloc group as the final protecting group and an active ester method for the coupling.
- 天然有機化合物討論会の論文
- 1991-09-07
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