Synthesis of the Trisaccharide Repeating Unit from Azospirillum brasilense Type Strain Sp7 and Its Effect on Plant Growth

doi:10.6023/cjoc201706036

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2929-2939.DOI: 10.6023/cjoc201706036 Previous Articles Next Articles

Articles

固氮螺菌重复三糖片段的化学合成及其对植物生长的影响

许一仁^a, 张建军^a, 董燕红^a, 谭伟明^b

a 中国农业大学理学院北京 100193;
b 中国农业大学农学院北京 100193

收稿日期:2017-06-27 修回日期:2017-07-28 发布日期:2017-08-16
通讯作者: 张建军, 谭伟明 E-mail:zhangjianjun@cau.edu.cn;tanwm@cau.edu.cn
基金资助:
国家科技支撑计划（No.2015BAK45B01）及国家自然科学基金（No.21172257）资助项目.

Synthesis of the Trisaccharide Repeating Unit from Azospirillum brasilense Type Strain Sp7 and Its Effect on Plant Growth

Xu Yiren^a, Zhang Jianjun^a, Dong Yanhong^a, Tan Weiming^b

a School of Science, China Agricultural University, Beijing 100193;
b College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193

Received:2017-06-27 Revised:2017-07-28 Published:2017-08-16
Contact: 10.6023/cjoc201706036 E-mail:zhangjianjun@cau.edu.cn;tanwm@cau.edu.cn
Supported by:
Project supported by the National Science and Technology Pillar Program of China (No. 2015BAK45B01) and the National Natural Science Foundation of China (No. 21172257).

1. Synthesis of the Trisaccharide Repeating Unit from Azospirillum brasilense Type Strain Sp7 and Its Effect on Plant Growth.PDF(1592KB)

Abstract

A natural trisaccharide α-D-rhamnopyanosyl-(1→3)-α-L-fucopyranosyl-(1→4)-β-D-xylopyranoside was synthesized from xylose glycoside donor, fucose glycoside donor and rhamnopyanosyl glycoside donor using α-D-xylopyranoside, β-L-fucopyranoside and α-D-rhamnopyranoside as the raw material respectively. This trisaccharide is a repeating-structure of the cell wall of the Azospirillum brasilense type strain Sp7. In the critical glycosylation reaction between rhamnopyanosyl glycoside donor and disaccharide receptor, full protected trisaccharide was regioselectivity builded. Streamlined the synthesis steps and the total yield of trisaccharide is 10% base on β-L-fucopyranoside. This route is suitable for mass preparation of target products. Preliminary determination of plant growth regulating activity of germination bed in sand culture showed that at 100 mg/L concen-tration, the trisaccharide raised the rate of emergence, the plant height and the leaf area by 11.0%, 13.1% and 87.8%, respectively. It was preliminarily concluded that this trisaccharide had certain plant growth regulating activity.

Key words: α-D-rhamnopyranoside, β-L-fucopyranoside, β-D-xylopyranoside, regioselective glycosylation reaction, Azospi-rillum brasilense

Cite this article

Xu Yiren, Zhang Jianjun, Dong Yanhong, Tan Weiming. Synthesis of the Trisaccharide Repeating Unit from Azospirillum brasilense Type Strain Sp7 and Its Effect on Plant Growth[J]. Chin. J. Org. Chem., 2017, 37(11): 2929-2939.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Truchet, G.; Roche, P.; Lerouge, P.; Vasse, J.; Camut, S.; De Billy, F.; Prome, J. C.; Denarie, J. Nature 1991, 86, 670.
[2] Long, S. R. Plant Cell 1996, 8, 1885.
[3] Fedonenko, Y. P.; Egorenkova, I. V.; Konnova, S. A.; Ignatov, V. V. Microbiology 2001, 70, 329.
[4] Jofre, E.; Lagares, A.; Mori, G. FEMS Microbiol. Lett. 2004, 231, 267.
[5] Wang, Y.; Hollingsworth, R. I. Carbohydr. Res. 1994, 260, 305.
[6] Russa, R.; Bruneteau, M.; Shashkov, A. S.; Urbanik-Sypniewska, T.; Mayer, H. Arch. Microbiol. 1996, 165, 26.
[7] Learemans, T.; Vanderleyden, J. World J. Microbiol. Biotechnol. 1998, 14, 787.
[8] Forsberg, L. S.; Carlson, R. W. J. Biol. Chem. 1998, 273, 2747.
[9] Zabotina, O. A.; Gurjanov, O. P.; Ibragimova, N. N.; Ayupova, D. A.; Lozovaya, V. V Plant Sci. 1998, 135, 195.
[10] Zhang, J.; Kong, F. J. Carbohydr. Chem.2002, 21, 579.
[11] Liu, H.; Cheng, S.; Liu, J.; Du, Y.; Bai, Z. J. Agric. Food Chem. 2008, 56, 5634.
[12] Tarrand, J. J.; Krieg, N. R.; Dobereiner, J. Can. J. Microbiol. 1978, 24, 967.
[13] Michiels, K.; Croes, C.; Vanderleyden, J. J. Gen. Microbiol. 1991, 137, 2241.
[14] Lerner, A.; Castro-Sowinski, S.; Valverde, A.; Lerner, H.; Dror, R.; Okon, Y.; Burdman, S. Microbiol-Sgm. 2009, 155, 4058.
[15] Van Puyvelde, S; Cloots, L; Engelen; K. Microb. Ecol. 2011, 61, 723.
[16] Zong, G.; Feng, Y.; Liang, X.; Chen, L.; Zhang, J.; Wang, D. Carbohydr. Res. 2010, 345, 2067.
[17] Sigida, E. N.; Fedonenko, Y. P.; Shashkov, A. S.; Zdorovenko, E. L.; Konnova, S. A.; Ignatov, V. V.; Knirel, Y. A. Carbohydr. Res. 2013, 380, 76.
[18] Zunk, M.; Kiefel, M. J. Tetrahedron Lett. 2011, 52, 1296.
[19] (a) Jiang, R.; Zong, G.; Liang, X.; Jin, S.; Zhang, J.; Wang, D. Molecules 2014, 19, 6683.
[20] Wang, J. Y.; Jiang, R.; Liang, X. M.; Wang, D. Q.; Zhang, J. J. Chin. J. Org. Chem. 2017, 37, 375(in Chinese). (王家尧, 姜锐, 梁晓梅, 王道全, 张建军, 有机化学, 2007, 37, 375.)
[21] Jiang, R.; Liang, X. M.; Sun, J.; Zhang, J. J.; Wang, D. Q. Chin. J. Org. Chem. 2014, 34, 926(in Chinese). (姜锐, 梁晓梅, 孙晋, 张建军, 王道全, 有机化学, 2014, 34, 926.)
[22] Zong, G.; Yu, N.; Xu, Y.; Zhang, J.; Wang, D.; Liang, X. Synthesis-Stuttgart 2010, 10, 1666.
[23] Ishiwata, A.; Sakurai, A.; Nishimiya, Y.; Tsuda, S.; Ito, Y. J. Am. Chem. Soc. 2011, 133, 19524.
[24] Helm, R. F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015.
[25] Zong, G. H.; Yan, S. Q.; Mei, X.; Liang, J.; Zhang, J.; Quan, D.; Fan, W.; Kong, Z. Chin. Chem. Lett. 2009, 20, 127.
[26] Morishima, N.; Koto, S.; Kusuhara, C.; Zen, S. Bull. Chem. Soc. Jpn. 1982, 55, 631.
[27] Mandal, P. K.; Dhara, D.; Misra, A. K. Synthesis-Stuttgart 2014, 46, 1947.
[28] Patro, B.; Schmidt, R. R. Synthesis-Stuttgart 1998, 12, 1731.

固氮螺菌重复三糖片段的化学合成及其对植物生长的影响

Synthesis of the Trisaccharide Repeating Unit from Azospirillum brasilense Type Strain Sp7 and Its Effect on Plant Growth

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments