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题名: 含唾液酸碳苷的寡糖纳米金粒子的合成与应用研究
作者: 张磊
学位类别: 博士
答辩日期: 2010
授予单位: 中国科学院研究生院
授予地点: 北京
导师: 杜宇国
关键词: Huisgen 1 ; 3-偶极环加成反应 ; 烯烃复分解反应 ; 唾液酸 ; 糖纳米金 ; 唾液酸碳苷 ; 芹菜素
中文摘要:       本文主要研究了含唾液酸碳苷的寡糖纳米金粒子的结构设计、化学合成及生物活性,同时探索了一种天然黄酮产物的全合成。全文共分六章: 第一章 综述了近年来非酶水解型唾液酸寡糖衍生物的合成研究进展,对非酶水解型唾液酸寡糖的由来、生物特性、化学修饰及对生物活性的影响做了简要介绍。 第二章 基于Cu(I)催化的Huisgen 1,3-偶极环加成反应,构建了Neu5Ac-α(2→3)-Gal连接的唾液酸复合物,并合成了其水溶性的纳米金粒子。 第三章 基于Grubbs-II 催化条件下发生的烯烃复分解反应,合成了亚甲基桥连的Neu5Ac-α(2→6)-Gal碳苷模拟物,并首次合成了其纳米金粒子,并经酶活性抑制检测表明,制备的碳苷纳米金粒子的酶抑制活性明显好于其唾液酸碳苷单体。 第四章 二碘化钐催化条件下,以唾液酸的硫砜为供体合成了羟亚甲基桥连的Neu5Ac-α(2→6)-Gal碳苷模拟物,并首次合成了其纳米金粒子,酶活性抑制检测表明,制备的碳苷纳米金粒子的酶抑制活性大大好于其唾液酸碳苷单体。 第五章 基于the 2nd generation Grubbs 催化条件下发生的烯烃复分解反应,合成了亚甲基桥连的Neu5Ac-α(2→3) -Gal碳苷模拟物。 第六章 以芹菜素和1,2-氧-亚乙基-α-D-葡萄糖为原料运用汇聚式合成策略,以7步35%的总产率首次合成了天然抗氧化剂芹菜素-4'-氧-(2"-氧-对羟基苯丙烯酰基)-β-D-葡萄糖苷。
英文摘要:       This dissertation is focusing on the structure design, chemical synthesis and bioactivity study of C-sialoside functionalized gold glyconanoparticles and total synthesis of natural product about flavonoids. Six chapters are included in the thesis: In Chapter one, Researches on the non-hydrolyzable sialic acid derivatives as neuraminidase inhibitors over the past few years were reviewed. In this chapter, the source, structure, bioactivity and chemical modify of the non-hydrolyzable sialic acid derivatives were introduced. In Chapter two, Neu5Ac-Gal-containing neoglycoside was convergently synthesized by using Cu(I)-catalyzed Huisgen1,3-dipolar cycloaddition reaction. The stable and water- soluble gold glyconanoparticle has been carefully prepared from neoglycoside. In Chapter three, The ethylene-bridged Neu5Ac-α(2→6)-Gal analogue was synthe sized using cross metathesis reaction, and the C-sialoside functionalized gold glyconan oparticle was firstly synthesized. These novel sialic acid derivatives were evaluated as potential neuraminidase inhibitors using a 96-well plate fluorescence assay and found the inhibitory activity of gold glyconanoparticle is much better than monomer. In Chapter four, The hydroxymethylene-bridged Neu5Ac-α(2→6)-Gal analogue was synthesized using Samarium chemistry, and the C-sialoside functionalized gold glyconanoparticle was firstly synthesized. These novel sialic acid derivatives were evaluated as potential neuraminidase inhibitors and found the inhibitory activity of gold glyconano particle is much better than monomer. In Chapter five, The ethylene-bridged Neu5Ac-α(2→3)-Gal analogue was synthe sized using cross metathesis reaction. In Chapter six, Apigenin-4'-yl 2-O-(p-coumaroyl)-β-D-glucopyranoside has been firstly synthesized from apigenin and 1,2-O-ethylidene-a-D-glucopyranose in 7 steps and 35% overall yield.
内容类型: 学位论文
URI标识: http://ir.rcees.ac.cn/handle/311016/35028
Appears in Collections:环境化学与生态毒理学国家重点实验室_学位论文

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Recommended Citation:
张磊. 含唾液酸碳苷的寡糖纳米金粒子的合成与应用研究[D]. 北京. 中国科学院研究生院. 2010.
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