基于硅胶负载高氯酸(HClO4-SiO2)的固氮螺菌四糖重复单元的高效合成

doi:10.6023/cjoc201911025

有机化学 ›› 2020, Vol. 40 ›› Issue (6): 1716-1724.DOI: 10.6023/cjoc201911025 上一篇下一篇

研究论文

基于硅胶负载高氯酸(HClO₄-SiO₂)的固氮螺菌四糖重复单元的高效合成

陈自力^a, 李培霞^a, 刘伟童^a, 庄喆^a, 武源源^a, 赵汗青^a, 张建军^b

a 北京农学院农业农村部华北都市农业重点实验室北京 102206;
b 中国农业大学理学院北京 100193

收稿日期:2019-11-20 修回日期:2020-01-22 发布日期:2020-02-15
通讯作者: 赵汗青, 张建军 E-mail:zhaohanqing@bua.edu.cn;zhangjianjun@cau.edu.cn
基金资助:
北京市自然科学基金（No.2194072）、国家自然科学基金（No.21772230）、北京市教育委员会科技计划一般项目（No.KM201710020003）、北京金桥工程种子基金（No.JQ18029）、北京农学院青年教师科研基金（No.SXQN201801）、北京农学院学位与研究生教育改革与发展项目（No.2019YJS028）和北京农学院内涵发展定额大学生科研训练（No.KX2019001）资助项目.

High Efficiency Synthesis of the Tetrasccharide Repeating Unit in Azospirillum brasilense Strains Sp246 Based on Silica Gel Supported Perchloric Acid (HClO₄-SiO₂)

Chen Zili^a, Li Peixia^a, Liu Weitong^a, Zhuang Zhe^a, Wu Yuanyuan^a, Zhao Hanqing^a, Zhang Jianjun^b

a Key Laboratory for Northern Urban Agriculture of Ministry of Agriculture and Rural Affairs, Beijing University of Agriculture, Beijing 102206;
b School of Science, China Agricultural University, Beijing 100193

Received:2019-11-20 Revised:2020-01-22 Published:2020-02-15
Supported by:
Project supported by the Natural Science Foundation of Beijing City (No. 2194072), the National Natural Science Foundation of China (No. 21772230), the General Plan of Beijing Education Commission (No. KM201710020003), the Seed Funding of Beijing Jinqiao Project (No. JQ18029), the Youth Foundation of Beijing University of Agriculture (No. SXQN201801), the Research Fund for Academic Degree & Graduate Education of Beijing University of Agriculture (No. 2019YJS028) and the Connotation Development Quota Scientific Research Training for College Students of Beijing University of Agriculture (No. KX2019001).

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摘要/Abstract

以2，3，4-三-O-苯甲酰基-α-L-鼠李糖三氯乙酰亚胺酯、2，4-二-O-苯甲酰基-α-L-鼠李糖对甲氧基苯基苷、2，3，4，6-四-O-苯甲酰基-β-D-葡萄糖三氯乙酰亚胺酯和2，3-O-异丙叉基-α-L-鼠李糖对甲氧基苯基苷为原料，采用[2+2]偶联策略，对巴西固氮螺菌（Azospirillum brasilense type strain Sp246）表面脂多糖的四糖重复单元α-L-鼠李糖-（1→3）-α-L-鼠李糖-（1→3）-[β-D-葡萄糖-（1→4）]-α-L-鼠李糖结构进行全合成.在合成单元子的反应中，采用硅胶负载高氯酸（HClO₄-SiO₂）作为酸性催化剂，三乙基硅基作为选择性保护基，简单高效地构建全保护的四糖.该合成路线步骤短，试剂种类少，反应后处理简单，以L-鼠李糖为原料计算，目标化合物四糖总收率达到23%，化合物结构经¹H NMR和¹³C NMR、HRMS和IR确证.

关键词: 鼠李糖, 硅胶负载高氯酸(HClO₄-SiO₂), 固氮螺菌, 寡糖合成

A natural tetrasaccharide of α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-[β-D-Glup-(1→4)-]α-L-Rhap was synthesized via [2+2] assembly from 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate, p-methoxyphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside, 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl trichloroacetimidate and p-methoxyphenyl 2,3-O-isopro-pyl-α-L-rhamnopyranoside. This tetrasaccharide is a repeating unit of the lipopolisaccharides of the nitrogen fixing bacterium Azospirillum brasilense Sp246. In the reaction of the synthesis unit, silica gel loaded perchloric acid (HClO₄-SiO₂) was used as acid catalyst, and triethylsilyl group was used as selective protective group to construct a fully protected tetrasaccharide. The synthetic route is short, the reagents are few, and the post-processing is simple. The total yield of target tetrasaccharide is 23% based on L-rhamnose. The structures of the tetrasaccharide were confirmed by ¹H NMR, ¹³C NMR, HRMS and IR spectra.

Key words: rhamnose, silica gel supported perchloric acid (HClO₄-SiO₂), Azospirillum brasilense, oligosaccharide synthesis

引用此文

陈自力, 李培霞, 刘伟童, 庄喆, 武源源, 赵汗青, 张建军. 基于硅胶负载高氯酸(HClO₄-SiO₂)的固氮螺菌四糖重复单元的高效合成[J]. 有机化学, 2020, 40(6): 1716-1724.

Chen Zili, Li Peixia, Liu Weitong, Zhuang Zhe, Wu Yuanyuan, Zhao Hanqing, Zhang Jianjun. High Efficiency Synthesis of the Tetrasccharide Repeating Unit in Azospirillum brasilense Strains Sp246 Based on Silica Gel Supported Perchloric Acid (HClO₄-SiO₂)[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1716-1724.

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基于硅胶负载高氯酸(HClO₄-SiO₂)的固氮螺菌四糖重复单元的高效合成

High Efficiency Synthesis of the Tetrasccharide Repeating Unit in Azospirillum brasilense Strains Sp246 Based on Silica Gel Supported Perchloric Acid (HClO₄-SiO₂)

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