摘要
2-氯-4-硝基苯基糖苷是一类重要的糖基酶底物试剂,在相关酶抑制剂制备、酶生物活性研究中有着广泛的应用。以D-半乳糖为原料,通过4步反应得到中间体D-岩藻糖;再经乙酰化制备1,2,3,4-三-O-乙酰基-α,β-D-吡喃岩藻糖,溴代反应获得1-溴-2,3,4-三-O-乙酰基-α-D-吡喃岩藻糖,通过溴代糖与2-氯-4-硝基苯酚偶联,立体选择性获得2-氯-4-硝基苯-2,3,4-三-O-乙酰基-β-D-吡喃岩藻糖基糖苷,最后脱除乙酰基保护得标题化合物。该化合物可以作为一种新型的β-D-岩藻糖苷酶底物试剂,用于酶活性测试,其合成方法未见文献报道。
2-Chloro-4-nitrophenyl as a very important fluorogenic group has been used for synthesis many glycoside enzyme substrates which are widely applied in the research of its related enzyme inhibitor sandenzyme activities.In this work,a novel compound 2-chloro-4-nitrophenyl-β-D-fucoside has been designed and synthesized as enzyme substrate for β-D-fucosidase.Firstly,Dfucose was synthesized from the commercially inexpensive D-galactose as the starting material in four steps.Secondly,1-bromo-2,3,4-tri-O-acetyl-α-D-fucoside was prepared from D-fucose via acetylization and bromination.Thirdly,the 1-bromo-2,3,4-tri-Oacetyl-α-D-fucoside was coupled to fluorescein 2-chloro-4-nitrophenol to obtain 2-chloro-4-nitrophenyl-2,3,4-tri-O-acetyl-β-D-fucoside in the way of stereoselectivity.At last,the target compound 2-chloro-4-nitrophenyl-β-D-fucoside was obtained from 2-chloro-4-nitrophenyl-2,3,4-tri-O-acetyl-β-D-fucoside via deacetylation.
作者
沈生强
张建军
SHEN Sheng-qiang ZHANG Jian-jun(Scientific Reagent Platform, College of Science, China Agricultural University, Beijing 100193, China)
出处
《化学试剂》
CAS
北大核心
2017年第3期305-308,共4页
Chemical Reagents
基金
国家十二五科技支撑计划"科研用试剂产业链创新体系的构建"资助项目(2015BAK45B01)
