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

doi:10.6023/cjoc201911025

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1716-1724.DOI: 10.6023/cjoc201911025 Previous Articles Next Articles

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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Abstract

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

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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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[1] (a) Camporese, G.; Bernardi, E. Curr. Opin. Pulm. Med. 2009, 15, 443.
(b) Hsu, C. H.; Hung, S. C.; Wu, C. Y.; Wong, C. H. Angew. Chem., Int. Ed. 2011, 50, 11872.
[2] Mrozik, H.; Eskola, P.; Linn, B. O. Experientia 1989, 45, 315.
[3] Hu, B. Y.; Zhao, H. Q.; Chen, Z. L.; Xu, C.; Zhao, J. Z.; Zhao, W. T. Molecules 2018, 23, 709.
[4] (a) Smeekens, S.; Ma, J.; Hanson, J. Curr. Opin. Plant Biol. 2010, 13, 274.
(b) Ciereszko, I. Acta Soc. Bot. Pol. 2018, 87, 3583.
[5] Shibuya, N.; Minami, E. Physiol. Mol. Plant Pathol 2001, 59, 223.
[6] (a) Chai, Y. H.; Feng, Y. L.; Wu, J. J.; Deng, C. Q.; Liu, A. Y.; Zhang, Q. Chin. Chem. Lett. 2017, 28, 1693.
(b) Hanessian, S.; Lou, B. Chem. Rev. 2000, 100, 4443.
(c) Jensen, K. J. Chem. Soc., Perkin Trans. 2 2002, 2219.
[7] Song, W. Z.; Wang, S. J.; Tang, W. P. Chem.-Asian J. 2017, 12, 1027.
[8] Fischer, E. Ber. Desch. Chem. Ges. 1893, 26, 2400.
[9] Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
[10] (a) Nielsen, M. M.; Pedersen, C. M. Chem. Rev. 2018, 118, 8285.
(b) Toshima, K.; Sasaki, K. Comprehensive Glycoscience, Vol. 1, Elsevier, Amsterdam, 2007, p. 261.
[11] (a) Khan, A. T.; Choudhury, L. H.; Ghosh, S. ChemInform 2006, 255, 230.
(b) Mohammad, A. B.; Nemati, F.; Mahdavinia, G. H. Tetrahedron Lett. 2007, 48, 6801.
(c) Yan, S. Q.; Zhang, W.; Ding, N.; Li, Y. X. Chin. J. Org. Chem. 2012, 32, 2081(in Chinese). (颜世强, 张伟, 丁宁, 李英霞, 有机化学, 2012, 32, 2081.)
(d) Chun, Y. X.; Yan, S. Q.; Li, X. P.; Ding N.; Zhang, W.; Wang, P.; Li, M.; Li Y. X. Tetrahedron Lett. 2011, 6196.
[12] (a) Sigida, E. N.; Fedonenko, Y. P.; Shashkov, A. S.; Toukach, P. V.; Shelud'ko, A. V.; Zdorovenko, E. L.; Knirel, Y. A.; Konnova, S. A. Int. J. Biol. Macromol. 2019, 126, 246.
(b) Zong, G. H.; Cai, X. Y.; Liang, X. M.; Zhang, J. J.; Wang, D. Q. Carbohydr. Res. 2011, 346, 2533.
[13] (a) Corsaro, M. M.; Castro, C. D.; Molinaro, A.; Parrilli, M. Recent Res. Dev. Phytochem. 2001, 5, 119.
(b) Ayers, A. R.; Ebel, J.; Valent, B. Plant. Phytopathol. 1976, 57, 760.
(c) Sigida, E. N.; Fedonenko, Y. P.; Shashkov, A. S.; Shelud'ko, A. V.; Zdorovenko, E. L.; Konnova, S. A.; Knirel, Y. A. Carbohydr. Res. 2019, 478, 54.
[14] (a) Bini, D.; Forcella, M.; Cipolla, L.; Fusi, P. Eur. J. Org. Chem. 2011, 23, 3995.
(b) Baldani, J. I.; Baldani, V. L. An. Acad. Bras. Cienc. 2005, 77, 549.
(c) Zong, G. H.; Liang, X. M.; Zhang, J. J.; Duan, L. S.; Tan, W. M.; Wang, D. Q. Carbohydr. Res. 2014, 388, 87.
[15] (a) Ibrahim, I. M.; Sigida, E. N.; Kokoulin, M. S.; Fedonenko, Y. P.; Konnova, S. A. Carbohydr. Res. 2019, 473, 1.
(b) Zhao, H. Q.; Jia, H. Q.; Duan, H. X.; Zhang, J. J.; Wang, D. Q.; Liang, X. M. J. Carbohydr. Chem. 2010, 29, 1.
(c) Prashant, R. V.; Balaram, M. Carbohydr. Res. 2010, 345, 432.
(d) Zong, G. H.; Feng, Y. C.; Liang, X. M.; Chen, L. Z.; Zhang, J. J.; Wang, D. Q. Carbohydr. Res. 2010, 345, 2067.
[16] (a) Sigida, E. N.; Fedonenko, Y. P.; Shashkov, A. S.; Grinev, V. S.; Zdorovenko, E. L.; Konnova, S. A.; Ignatov, V. V.; Knirel, Y. A. Carbohydr. Res. 2014, 398, 40.
(b) Fedonenko, Y. P.; Sigida, E. N.; Konnova, S. A.; Ignatov, V. V. Russ. Chem. Bull. 2015, 64, 1024.
[17] Yan, S. Q.; Ding, N.; Zhang, W.; Wang, P.; Li Y. X.; Li, M. Carbohydr. Res. 2012, 354, 6.
[18] (a) Daniel, B. W.; Peter, H. S. Angew. Chem. 2005, 44, 6315.
(b) Cai, X. Y.; Zong, G. H.; Xu, Y. J.; Zhang, J. J.; Liang, X. M.; Wang, D. Q. Carbohydr. Res. 2010, 345, 1230.
(c) Xiong, J. L.; Yan, S. Q.; Ding, N.; Zhang, W.; Li, Y. X. J. Carbohydr. Chem. 2013, 32, 184.
[19] Charles, G.; Jean, L.; Maxime, L.; Philippe, D.; Andre, P. Bioorg. Med. Chem. 2006, 14, 6713.
[20] Kakali, S.; Indrani, M.; Nirmolendu, R. J. Carbohydr. Chem. 2011, 22, 95.

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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[1]	Yang Weizhun, Li Rongyao, Han Wei, Zhang Weidong, Sun Jiansong. Highly Efficient Synthesis of Kaempferol-5-O-rhamnopyranoside [J]. Chin. J. Org. Chem., 2012, 32(06): 1067-1071.
[2]	CHEN Lang-Qiu^,1,2,LAI Duan, SONG Zhi-Wei ZHAO Xing-E,KONG Fan-Zuo^,2. Strategies on Stereoselective Synthesis of Oligosaccharides [J]. Chin. J. Org. Chem., 2006, 26(05): 627-642.
[3]	Miao Zhenchun;Zhou Yongxin;Feng Rui;Wei Feng. Structural determniation of A new bidesmosidic triterpenoid glycoside from dipsocus japonicus [J]. Chin. J. Org. Chem., 2000, 20(1): 81-87.
[4]	ZHANG SANQI;LI ZHONGJUN;WANG ANBANG;CAI MENGSHEN;FENG RUI. Synthesis of three protective phenylpropanoid glycosides [J]. Chin. J. Org. Chem., 1997, 17(6): 529-534.
[5]	KONG FANZUO. Improved synthesis of 1,3-anhydro-2,4-di-O-benzyl- β-L-rhamno-pyranose and 1,3-anhydro-2,4,6-tri-O-benzyl- β-D-mannopyranose [J]. Chin. J. Org. Chem., 1994, 14(3): 280-285.
[6]	HU YOUCHUAN. Structure determination of the sugar component in calonyctin A [J]. Chin. J. Org. Chem., 1989, 9(2): 141-145.
[7]	HU YOUCHUAN;GUO QIZHEN. Structure determination of calonyctin A1 and calonyctin A2 [J]. Chin. J. Org. Chem., 1989, 9(2): 146-150.

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