Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein

doi:10.6023/cjoc201610045

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1814-1823.DOI: 10.6023/cjoc201610045 Previous Articles Next Articles

Articles

具有叶绿素碳架的二氢卟吩醛的合成及其与蛋白质的结合作用

姜齐永^a, 张珠^a, 刘洋^b, 姚楠楠^b, 王进军^a,b

a. 烟台大学文经学院食品与生物工程系烟台 264005;
b. 烟台大学化学化工学院烟台 264005

收稿日期:2016-10-31 修回日期:2017-01-16 发布日期:2017-03-03
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
国家自然科学基金（No.21272048）和山东省高校科技计划（No.J15LC51）资助项目.

Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein

Jiang Qiyong^a, Zhang Zhu^a, Liu Yang^b, Yao Nannan^b, Wang Jinjun^a,b

a. Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005;
b. College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received:2016-10-31 Revised:2017-01-16 Published:2017-03-03
Contact: 10.6023/cjoc201610045 E-mail:wjj1955@163.com
Supported by:
Project supported by the National Natural Science Foundations of China (No.21272048) and the University Science and Technology Plan Projects of Shandong Province (No.J15LC51).

1. Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein.PDF(3754KB)

Abstract

Pyropheophorbide-a (b) methyl esters were used as starting materials to form different chlorophyll degradation products by the modification of the exocyclic ring and the metallization of the chromophore. The new functional groups were introduced at 20-position via the Vilsmeier acylation and the Blanc hydroxymethylation. The active structures of chlorin peripheries were oxidized using osmium tetroxide, thaillum nitrate and air as oxidizing agent to introduce the formyl group and the formylmethyl group at 3-, 7-or 12-postion and on the exocyclic ring, respectively. A series of unreported chlorin aldehydes related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and ¹H NMR spectra. The reaction mechanisms on the hydroformylation for the chlorophyllous chlorins were discussed and the interactions of new compounds with bovine serum albumins were researched.

Key words: chlorophyll, chlorin, bovine serum albumins, chemical modification, florescence quenching

Cite this article

Jiang Qiyong, Zhang Zhu, Liu Yang, Yao Nannan, Wang Jinjun. Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein[J]. Chin. J. Org. Chem., 2017, 37(7): 1814-1823.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Nyman, E. S.; Hynninen, P. H. J. Photochem. Photobiol. A 2004, 73, 1.
(b) Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
(c) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353(in Chinese). (王进军, 有机化学, 2005, 25, 1353.)
(d) Goswami, L. N.; Ethirajan, M.; Dobhal, M. P.; Zhang, M.; Missert, J. R.; Shibata, M.; Kadish, K. M.; Pandey, R. K. J. Org. Chem. 2009, 73, 568
[2] (a) Okamoto, Y.; Tamiaki, H. J. Photochem. Photobiol. A 2011, 209, 250.
(b) Li, J.; Liu, Y.; Xu, X.-S.; Li, Y.-L.; Zhang, S.-G.; Yoon, I.; Shim, Y.K.; Wang, J.-J.; Yin, J.-G. Org. Biomol. Chem. 2015, 13, 1992.
(c) Li, Y.-L.; Li, J.-Z.; Zhang, S.-G.; Wang, J.-J. Chin. J. Org. Chem. 2016, 36, 562(in Chinese). (李彦龙, 李家柱, 张善国, 王进军, 有机化学, 2016, 36, 562.)
(d) Li, J.; He, N.; Liu, Y.; Zhang, Z.; Zhang, X.; Han, X.; Gai, Y.; Liu, Y.; Yin, J.; Wang, J. Dyes Pigm. 2017, 146, 189.
[3] (a) Li, J.-Z.; Wang, J.-J.; Yoon, I.; Cui, B.-C.; Shim, Y. K. Bioorg. Med. Chem. Lett. 2012, 22, 1846.
(b) Liu, H.-Y.; Zhu, G.-H.; Liu, Y.-Y.; Jin, Y.-X.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2015, 35, 1320(in Chinese). (刘红瑶, 朱国华, 刘冉冉, 金英学, 祁彩霞, 王进军, 有机化学, 2015, 35, 1320.)
[4] Ali, H.; Vanlier, J. E. In Handbook of Porphyrin Science, Vol. 4, Eds.:Kadish, K. M.; Smith, K. M.; Guilard, R., World Scientific Publishing Company, Singapore, 2010, pp. 1~119.
[5] Ethirajan, M.; Patel, N. J.; Pandey, R. K. In Handbook of Porphyrin Science, Vol. 4, Eds.:Kadish, K. M.; Smith, K. M.; Guilard, R., World Scientific Publishing Company, Singapore, 2010, pp. 249~323.
[6] Wang, X. F.; Tamiaki, H. Energy Environ. Sci. 2010, 3, 94
[7] (a) Yin, J.-G.; Wu, X.-R.; Liu, C.-L.; Zhao, L.-L., Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2011, 31, 1870(in Chinese). (殷军港, 邬旭然, 刘春林, 赵丽丽, 金英学, 王进军, 有机化学, 2011, 31, 1870.)
(b) Yin, J.-G.; Wang, Z.; Yang, Z.; Liu, C.; Zhao, L.-L.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 360(in Chinese). (殷军港, 王振, 杨泽, 刘超, 赵丽丽, 金英学, 王进军, 有机化学, 2012, 32, 360.)
[8] (a) Wang, J.-J.; Shim, Y. K.; Jiang, G.-J.; Imafuku, K. J. Heterocycl. Chem. 2004, 41, 29.
(b) Wang, J.-J.; Li, J.-Z.; Wu, X.-R.; Shim, Y. K. Chin. J. Chem. 2006, 24, 933.
[9] (a) Wang, L.-M.; Wang, Z.; Yang, Z.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 2154(in Chinese). (王鲁敏, 王振, 杨泽, 金英学, 王进军, 有机化学, 2012, 32, 2154.)
(b) Ji, J.-Y.; Xia, S.-W.; Liu, Y.; Yin, J.-G.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34, 1138(in Chinese). (纪建业, 夏尚文, 刘洋, 殷军港, 祁彩霞, 王进军, 有机化学, 2014, 34, 1138.)
[10] Liu, Y. M.S. Thesis, Yantai University, Yantai, 2014(in Chinese). (刘洋, 硕士论文, 烟台大学, 烟台, 2014.)
[11] (a) Hu, X.-L.; Cui, S.-Y.; Liu, J.-Q. Spectrochim. Acta A 2010, 77, 548.
(b) Jia, F.-G.; Wang, W.-W.; Wang, J.; Yin, J.-G.; Liu, Y.-M.; Liu, Z.-B. Anal. Methods 2012, 4, 449.
[12] (a) Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
(b) Schenk, J.; Daessler, H. G. Pharmazie 1969, 24, 419.

[1]	Jiantao Zhang, Cong Zhang, Nuolin Mo, Jiating Luo, Lianfen Chen, Weibing Liu. Research Progress in Radical Addition Reaction of Alkenes Involving Chloroform [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3098-3106.
[2]	Fen Huang, Weiwei Luo, Jun Zhou. Research Progress of Polychloroalkylation Based on C—H Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2368-2390.
[3]	Na Gao, Xiaohui Chu, Yang Liu, Jiazhu Li, Jinjun Wang. Regio- and Stereoselective Aryl(aroyl)methylenenation of Pyropheophorbide and Syntheses of Chlorophyllous Chlorin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1111-1122.
[4]	Yun Zhao, Yanfang Li, Rongxiao Li, Yaqing Wang, Xiaoxia Fan. A New Fluorescent Probe for Hypochlorous Acid Based on Chlorinium Ions Recognition Mechanism and Its Bioimaging Research in Living Cells [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1974-1981.
[5]	Zhu Zhang, Yu Zhao, Xinyue Wang, Jiazhu Li, Jinjun Wang. Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1177-1186.
[6]	Yaoxin Wang, Chen Cui, Xiaohui Yang. Recent Advances in Hydrochlorination of Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3808-3815.
[7]	Zhang Zhu, Li Jiazhu, Wang Xinyue, Ma Jihua, Wang Xu, Wang Jinjun. Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2895-2903.
[8]	Zhu Ye, Huang Jinwen, Yang Xianjin. Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide [J]. Chin. J. Org. Chem., 2019, 39(6): 1665-1671.
[9]	Zong Wuzhong, Hu Yulai, Wang Xiaoping, Liu Jiaxin, Huang Danfeng, Wang Kehu. Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source [J]. Chin. J. Org. Chem., 2019, 39(5): 1396-1403.
[10]	Su Yingpeng, Shi Ya, Chang Bingbing, Wu Lili, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source [J]. Chin. J. Org. Chem., 2018, 38(6): 1454-1461.
[11]	Zhang Zhu, Li Jiazhu, Zhang Shanguo, Wang Zhen, Wang Jinjun. Heterocyclization for the Structures on the Periphery of Py-ropheophorbide and Synthesis of Chlorophyll Derivatives [J]. Chin. J. Org. Chem., 2018, 38(12): 3250-3259.
[12]	Liu Lifen, Zhang Xiao, Xie Xin, Li Ruihan, Gao Congjie. Modification of Polyimide-Urethane Reverse Osimosis Composite Membrane Based on NaA Zeolite [J]. Chin. J. Org. Chem., 2018, 38(11): 3127-3136.
[13]	Zhang Zhu, Xu Xisen, Li Yanlong, Li Jiazhu, Wang Jinjun. Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives [J]. Chin. J. Org. Chem., 2018, 38(11): 2993-3001.
[14]	Ren Shaobo, Zhang Haifeng, Zhang Jian, Zhang Wei, Liu Yunkui. Dichlorinating Reaction of N-Chlorosuccinimide with Isonitriles for the Synthesis of N-Phenyldichloroimides [J]. Chin. J. Org. Chem., 2016, 36(8): 1954-1957.
[15]	Chen Xiaowei, Chong Siying, Du Ganggang, Huang Danfeng, Wang Kehu, Su Yingpeng, Hu Yulai. Diacetoxyiodobenzene Promoted Chlorination of Silyl Enol Ether of Aryl Ketones [J]. Chin. J. Org. Chem., 2016, 36(5): 1028-1033.

具有叶绿素碳架的二氢卟吩醛的合成及其与蛋白质的结合作用

Synthesis of Chlorin Aldehydes with Chlorophyllous Skeleton and Their Interactions with Protein

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments