正交设计法优化炭疽杆菌表面糖抗原关键中间体二糖化合物的合成工艺

发布时间：2018-10-05 15:19

【摘要】：正炭疽杆菌表面糖抗原(图1)是炭疽杆菌细胞荚膜的主要成分~([1]),炭疽杆菌表面糖抗原的人工合成对炭疽疫苗的研发具有重大意义~([2])。1-叔丁基二苯基硅烷基-2-叠氮-3-O-(α-四-O-苄基-1-氧代-β-D-吡喃半乳糖基)-4,6-O-对甲氧基苄基-β-D-吡喃葡萄糖苷(1)是化学合成炭疽杆菌表面糖抗原的重要中间体。同类β-硫苷糖基化得到的1,3位连接的二糖产物为α、β构型混合物,α构型产率基本维持在17%~54%~([3-5]),由于本研究中单糖受体上的保护基位阻较大,导致路线(图2)中的二糖化合物(1)的预实验产率仅为21.1%,大大阻
[Abstract]:The surface sugar antigen of Bacillus anthracis (fig. 1) is the main component of Bacillus anthracis cell capsule ~ ([1]). The artificial synthesis of surface sugar antigen of Bacillus anthracis is of great significance to the development of anthrax vaccine ~ ([2]) .1-Tertiary Ding Ji diphenylsilyl -2-azido-3-O- (伪 -) Tetra-O-benzyl-1-oxo-beta-D-galactosyl) -46-O- p-methoxybenzyl- 尾 -D- glucopyranoside (1) is an important intermediate for the chemical synthesis of surface sugar antigen of Bacillus anthracis. The congener 尾 -thiosylglycosylation product was a mixture of 伪 and 尾 configuration, and the yield of 伪 configuration was maintained at 17554 ~ ([3-5]). Because of the large steric resistance of the monosaccharide receptor in this study, the product of 尾 -glucosinylation was a mixture of 伪 and 尾 configuration, and the yield of 伪 -glucosinylation was maintained at 17 ~ (-5) ~ (3 ~ 5). The experimental yield of disaccharide compound (1) in the route (Fig. 2) was only 21.1kW, which was greatly hindered.
【作者单位】：第二军医大学药学院有机化学教研室;
【基金】：国家科技重大专项(2012ZX09502001-005,20112XJ0901-012) 国家自然科学基金(21202200)~~
【分类号】：R914

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