Synthesis and Enzyme Substrate Activity of p-Nitrophenyl N,N'-Diacetyl-4-thio-β-chitobioside

doi:10.6023/cjoc201906008

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3490-3497.DOI: 10.6023/cjoc201906008 Previous Articles Next Articles

4-硝基苯基N,N'-二乙酰基-4-硫基-β-壳二糖苷的合成与酶底物活性研究

郭兵博, 沈生强, 金淑惠, 路慧哲, 张建军

中国农业大学理学院北京 100193

收稿日期:2019-06-10 修回日期:2019-07-31 发布日期:2019-08-07
通讯作者: 金淑惠, 张建军 E-mail:zhangjianjun@cau.edu.cn;shuhuij@cau.edu.cn
基金资助:
国家自然科学基金（No.21772230）及中国高校科研基金（No.2019TC135）资助项目.

Synthesis and Enzyme Substrate Activity of p-Nitrophenyl N,N'-Diacetyl-4-thio-β-chitobioside

Guo Bingbo, Shen Shengqiang, Jin Shuhui, Lu Huizhe, Zhang Jianjun

School of Science, China Agricultural University, Beijing 100193

Received:2019-06-10 Revised:2019-07-31 Published:2019-08-07
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21772230) and the Chinese Universities Scientific Fund (No. 2019TC135).

1. .pdf(1061KB)

Abstract

Based on the resistance of glycosidase to the hydrolysis of glycosidase, the probe molecule p-nitrophenyl N,N'-diacetyl-4-thio-β-chitobioside (pNP-TCB) was designed and synthesized. The effects of pNP-TCB on the degradation of glycoside hydrolase family 18 (GH18) chitinase and 20 (GH20) β-N-acetylhexosaminidase were studied. The results showed that when pNP-TCB was combined with β-N-acetylhexosaminidase, the disaccharide substrate was hardly degraded. But when it reacted with chitinase, the pNP-TCB was degraded by enzyme to release p-nitrophenol group, and the corresponding ultraviolet absorption value can be detected by enzyme-labeled instrument at 405 nm. It indicates that the substrate molecule exhibits good specificity, which can be used to study the properties of GH18 chitinase at the cellular level without interference of β-N-acetylhexosaminidase. The pNP-TCB can also provide a good detection method for screening and isolation between the GH18 chitinase and the GH20 β-N-acetyl hexose.

Key words: p-nitrophenol, disaccharide substrate, chitobioside, chitinase, UV absorption

Cite this article

Guo Bingbo, Shen Shengqiang, Jin Shuhui, Lu Huizhe, Zhang Jianjun. Synthesis and Enzyme Substrate Activity of p-Nitrophenyl N,N'-Diacetyl-4-thio-β-chitobioside[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3490-3497.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Lai, K. P. Pharm. Today 2009, 19, 14(in Chinese). (赖坤平, 今日药学, 2009, 19, 14.)
[2] Zhu, K. Y.; Merzendorfer, H.; Zhang, W. Annu. Rev. Entomol. 2016, 61, 177.
[3] Zechmeister, L.; Toth, G. Z. Physiol. Chem. 1934, 223, 53.
[4] Liu, T. Ph.D. Dissertation, Dalian University of Technology, Dalian, 2009 (in Chinese). (刘田, 博士论文, 大连理工大学, 大连, 2009.)
[5] Dahiya, N.; Tewari, R.; Hoondal, G. S. Appl. Microbiol. Biotechnol. 2006, 71485, 773.
[6] Alton, M. Adv. Enzymol. Relat. Areas Mol. Biol. 1987, 59, 59.
[7] Liu, T.; Chen, L.; Ma, Q.; Shen, X.; Yang, Q. Curr. Pharm. Des. 2014, 20, 754.
[8] Macdonald, J. M.; Tarling, C. A.; Taylor, E. J.; Dennis, R. J.; Myers, D. S.; Knapp, S.; Davies, G. J.; Withers, S. G. Angew. Chem., Int. Ed. 2010, 49, 2599.
[9] Chen, L.; Liu, T.; Duan, Y. J. Agric. Food Chem. 2017, 65, 3851.
[10] Schüttelkopf, A. W.; Andersen, O. A.; Rao, F. V. ACS Med. Chem. Lett. 2011, 2, 428.
[11] Dong, L. L.; Shen, S. Q.; Chen, W.; Lu, H. Z. Bioorg. Med. Chem. 2019, 27, 2135
[12] Shen, S. Q.; Chen, W.; Dong, L. L. J. Enzyme Inhib. Med. Chem. 2018, 33, 445.
[13] Shen, S. Q.; Dong, L. L.; Chen, W. J. Agric. Food Chem. 2019, 67, 6387.
[14] Boller, T.; Mauch, F. Methods Enzymol. 1988, 161, 430.
[15] Ohtakara, A. Methods Enzymol. 1988, 161, 426.
[16] Cabib, E. Methods Enzymol. 1988, 161, 424.
[17] Koga, D.; Yoshioka, T. Agric. Biol. Chem. 1998, 62, 1643
[18] Zhou, J. S.; Chen, L. L.; Kang, L. Q.; Liu, Z. H.; Yuan, S. J. Agric. Food Chem. 2018, 66, 12773.
[19] Duivenvoorden, B. A.; Ghauharali, K.; Scheij, S. Carbohydr. Res. 2014, 399, 26.
[20] Dong, L. L.; Shen, S. Q.; Lu, H. Z.; Jin, S. H.; Zhang, J. J. ACS Sens. 2019, 45, 1222.
[21] Krolicka, M.; Hinz, S. W. A.; Koetsier, M. J. J. Agric. Food Chem. 2018, 66, 1658.
[22] Van, Munster. J. M.; Dobruchowska, J. M.; Veloo, R. Appl. Microbiol. Biotechnol. 2015, 99, 2209.
[23] Wang, S.; Moyne, A. L.; Thottappilly, G.; Wu, S. J.; Locy, R. D.; Singh, N. K. Enzyme Microb. Technol. 2001, 28, 492.
[24] Rich, J. R.; Dr, A. S.; Dr, M. M. P. Angew. Chem. 2004. 116, 623.
[25] Driguez, H. ChemBioChem 2001, 2, 311
[26] Xu, Y. R.; Zhang, J. J.; Dong, Y. H.; Tan, W. M. Chin. J. Org. Chem. 2017, 37, 2929(in Chinese). (许一仁, 张建军, 董燕红, 谭伟明, 有机化学, 2017, 37, 2929.)
[27] Jiang, R.; Zong, G.; Liang, X.; Jin, S.; Zhang, J.; Wang, D. Molecules 2014, 19, 6683
[28] 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.)
[29] 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, 2017, 37, 375.)
[30] Wang, L. X.; Lee, Y. C. J. Chem. Soc. 1996, 27, 581.
[31] Chen, H. M.; Withers, S. G. Carbohydr. Res. 2007, 342, 2212.
[32] Davis, B. G. EP 1644390 2005[Chem. Abstr. 2005, 142, 94064].
[33] Chupakhina, T. A. Russ. J. Bioorg. Chem. 2004, 30, 301.
[34] Loft, K. J. ChemBioChem 2009, 10, 565.
[35] Nikolaev, A. V.; Ivanova, I. A.; Shibaev, V. N. Bioorg. Khim. 1990, 16, 1693.
[36] Fettke, A.; Peikow, D.; Peter, M. G. Tetrahedron 2009, 65, 4356.
[37] Nawani, N. N.; Kapadnis, B. P. J. Appl. Microbiol. 2010, 90, 803.
[38] Nguyen, H. A.; Nguyen, T. H. J. Agric. Food Chem. 2012, 60, 3475.

4-硝基苯基N,N'-二乙酰基-4-硫基-β-壳二糖苷的合成与酶底物活性研究

Synthesis and Enzyme Substrate Activity of p-Nitrophenyl N,N'-Diacetyl-4-thio-β-chitobioside

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 4

Recommended Articles

Metrics

Comments

[1]	Gu Guangna, Sun Huailin, Zhou Xiuzhong. Interaction of Silicon-Silicon Bonds and Phenyl Rings: UV Absorption Properties of Unsymmetrically Substituted 1,2 Diphenyltetramethyldisilanes [J]. Chin. J. Org. Chem., 2014, 34(2): 349-354.
[2]	LI Cui-Hong, SHEN Tian-Hua, CHEN Xiao-Li, ZHOU Cai-Qi, ZHANG Cheng, SONG Qing-Bao. Synthesis, Characterization and Properties of Aza-BODIPY Fluo-rescent Dyes [J]. Chin. J. Org. Chem., 2011, 31(9): 1440-1444.
[3]	HU Wei-Bing, FENG Fu, LI Yun-Pan, ZHOU Hong-Yan, WANG Hui, TIAN Da-Ting. Microwave-Assisted Knoevenagel Reaction of 2-Nitrofluorene with Aromatic Aldehyde [J]. Chin. J. Org. Chem., 2011, 31(06): 897-900.
[4]	HONG, Yong^a ; XIAO, Jing-Yi ^a; CHEN, Shi-Ping ^b ; WANG, Wei-Ling ^a ; HUANG, Ke-Long^*,a . Synthesis of Substituted Aromatic Aldehydes Bis-Schiff Bases and Their Spectrum Properties [J]. Chin. J. Org. Chem., 2008, 28(08): 1404-1409.