Solid Phase Synthesis and Property of Signature Motif Ⅲ in Peptide Transporter

doi:10.6023/cjoc201708053

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (1): 266-271.DOI: 10.6023/cjoc201708053 Previous Articles Next Articles

Special Issue: 庆祝吴养洁院士九十华诞专辑

Notes

寡肽转运蛋白特征基元III的固相合成与性质研究

赵东欣^a, 吕名秀^b, 马丽^a, 卢奎^a,b

a 河南工业大学化学化工与环境学院郑州 450001;
b 河南工程学院材料与化学工程学院郑州 450007

收稿日期:2017-08-24 修回日期:2017-10-11 发布日期:2017-10-16
通讯作者: 赵东欣, 卢奎 E-mail:zhaodx798@163.com;luckyluke@126.com
基金资助:
国家自然科学基金（Nos.21572046，21172054）和河南省科技攻关（No.162102210197）资助项目.

Solid Phase Synthesis and Property of Signature Motif Ⅲ in Peptide Transporter

Zhao Dongxin^a, Lü Mingxiu^b, Ma Li^a, Lu Kui^a,b

a School of Chemistry, Chemical Engineering and Environment, Henan University of Technology, Zhengzhou 450001;
b School of Material and Chemical Engineering, Henan University of Engineering, Zhengzhou 450007

Received:2017-08-24 Revised:2017-10-11 Published:2017-10-16
Contact: 10.6023/cjoc201708053 E-mail:zhaodx798@163.com;luckyluke@126.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572046, 21172054) and the Foundation of Scientific and Technological Project of Henan Province (No. 162102210197).

The peptide transporter family in human body is critical for the transport of peptides and drugs, and the conservative sequences in the peptide transporters play an important role in maintaining its structure and function. In order to understand the function of consensus peptides in peptide transporter and promote the application of oligopeptides in pharmaceutical and medical fields, the signature motif Ⅲ (FYLSINAGS) and its four mutants were synthesized by Fmoc solid phase synthesis method. The products were identified using mass spectrometry, and purified by RP-HPLC. The interaction between peptide and DNA was detected by UV and fluorescence spectrometry. The experimental and structural simulation results showed that the dominant role of electrostatic interaction and intercalation between oligopeptide FYLSINAGG and DNA was related to the concentration of oligopeptide FYLSINAGG, the interaction of FYGLINAGG containing helix structure and DNA was enhanced for the generation of complex, and the interaction between FYGLINKGG hasing helix structure or FYGLINSGG and DNA was attenuated. These results indicated that the serine residue in C-terminal of FYGSINAGS, and the number and position of serine in peptides had great influence on the structure of oligopeptide and its interaction with DNA. The mutation of serine into hydrophobic amino acids is beneficial to form helical structure of oligopeptides and enhance the embedded intercalation with DNA. Thus, serine residues in signature motif are important functional residues, especially at the C-terminus.

Key words: oligopeptide, solid phase synthesis, interaction, signature motif

Cite this article

Zhao Dongxin, Lü Mingxiu, Ma Li, Lu Kui. Solid Phase Synthesis and Property of Signature Motif Ⅲ in Peptide Transporter[J]. Chin. J. Org. Chem., 2018, 38(1): 266-271.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Frazer, K. A.; Sheehan, J. B.; Stokowski, R. P.; Chen, X.; Hosseini, R.; Cheng, J. F.; Fodor, S. P.; Cox, D. R.; Patil, N. Genome Res. 2001, 11, 1651.
(b) Bejerano, G.; Pheasant, M.; Makunin, I.; Stephen, D.; Kent, W. J.; Mattick, J. S.; Haussler, D. Science 2004, 304, 1321.
(c) Fire, A.; Xu, S.; Montgomery, M. K.; Kostas, S. A.; Driver, S. E.; Mello, C. C. Nature 1998, 391, 806.
(d) Florence, W.; Magdalena, Z. G. Nat. Cell Biol. 2000, 2, 70.
[2] (a) Ocheltree, S. M.; Keep, R. F.; Shen, H.; Yang, D. L.; Hughes, B. A.; Smith D. E. Pharmacol. Res. 2003, 20, 1364.
(b) Zhao, D. X.; Lu, K. Biosci. Trends 2015, 9, 207.
(c) Smith, D. E.; Clémencon, B.; Hediger, M. A. Mol. Aspects Med. 2013, 34, 323.
(d) Charrière, G. M.; Eddie Ip, W. K.; Dejardin, S.; Boyer, L.; Sokolovska, A.; Cappillino, M. P.; Cherayil, B. J.; Podolsky, D. K; Kobayashi, K. S.; Silverman, N.; Lacy-Hulbert, A.; Stuart, L. M. J. Biol. Chem. 2010, 285, 20147.
(e) Fei, Y. J.; Liu, W.; Prasad, P. D.; Kekuda, R.; Oblak, T. G.; Ganapathy, V.; Leibach, F. H. Biochemistry 1997, 36, 452.
[3] (a) Daniel, H.; Kottra, G. Pflug. Arch. Eur. J. Phy. 2004, 447, 610.
(b) Gindullis, F.; Rose, A.; Patel, S.; Meier, I. BMC Genomics 2002, 3, 9.
(c) Li, S. B; Qian, Q.; Fu, Z. M.; Zeng, D. L.; Meng, X. B.; Kyozuka, J.; Maekawa, M.; Zhu, X. D.; Zhang, J.; Li, J. Y.; Wang, Y. H. Plant J. 2009, 58, 592.
[4] (a) Cai, C. Q.; Chen, X. M.; Ge, F. Spectrochim. Acta A 2010, 76, 202.
(b) Zhao, D. X.; Ma, L.; Lu, K. Lett. Org. Chem. 2015, 12, 459.
(c) Wu, J. H.; Wei, L.; Zhao, M.; Wang, Y. J.; Kang, G. F.; Peng, S. Q. Med. Chem. Res. 2012, 21, 116.
(d) Li, N.; Ma, Y.; Yang, C.; Guo, L. P.; Yang, X. R. Biophys. Chem. 2005, 116, 199.
(e) Iwasaki, Y.; Kimura, M.; Yamada, A.; Mutoh, Y.; Tateishi, M.; Arii, H. Inorg. Chem. Commun. 2011, 14, 1461.
[5] (a) Shen, Y.; Maupetit, J.; Derreumaux, P.; Tufféry, P. J. Chem. Theory Comput. 2014, 10, 4745.
(b) Maupetit, J.; Derreumaux, P.; Tufféry, P. Nucleic Acids Res. 2009, 37, 498.
[6] (a) Long, E. C.; Barton, J. K. Acc. Chem. Res. 1990, 23, 271.
(b) Zhou, C. Y.; Zhao, Y.; Wu, Y. B.; Yin, C. X.; Yang, P. J. Inorg. Biochem. 2007, 101, 10.
(c) Guo, Q.; Li, L. Z.; Dong, J. F.; Liu, H. Y.; Xue, Z. C.; Xv, T. Acta Chim. Sinica 2012, 70, 1617(in Chinese).(郭琼, 李连之, 董建方, 刘鸿雁, 薛泽春, 许涛, 化学学报, 2012, 70, 1617.)
[7] (a) Gao, E. J.; Zhu, M. C.; Yin, H. X.; Liu, L.; Wu, Q.; Sun, Y. G. J. Inorg. Biochem. 2008, 102, 1958.
(b) Zhao, D. X.; Ma, L.; Lu, K.; Wu, J. Z.; He, J. Res. Chem. Intermediat 2015, 41, 8591.
(c) Chen, D. D.; Wu, Q.; Wang, J.; Wang, Q.; Qiao, H. Spectrochim. Acta A 2015, 135, 511.
(d) Guo, Y.; Liiu, B. S.; Li, Z. Y.; Zhang, L. H.; Lv, Y. K. Chin. J. Lumin. 2014, 35, 1114(in Chinese).(郭莹, 刘保生, 李志云, 张丽惠, 吕运开, 发光学报, 2014, 35, 1114.)
(e) Li, H.; Le, X. Y.; Wu, J. Z.; Liu, J.; Ji, L. N.; Jiang, X.; Li, W. S.; Xu, Z. H. Acta Chim. Sinica 2003, 61, 245.
[8] (a) Geng, S. G.; Cui, Y. R.; Liu, Q. F. J. Lumin. 2013, 141, 144.
(b) Zhao, D. X.; Lu, K. Heterocycles 2016, 92, 252.
(c) Muro, P. D.; Beltramini, M.; Nikolov, P.; Retkova, I.; Salvato, B.; Ricchelli, F. Z. Naturforsch. B 2002, 57, 1084.
[9] (a) Zhao, D. X; Lu, K. J. Mol. Model. 2015, 21, 299.
(b) Pires, D. A. T.; Bemquerer, M. P.; Nascimento, C. J. D. Int. J. Pept. Res. Ther. 2014, 20, 53.
(c) Amblard, M.; Fehrentz, J. A.; Martinez, J.; Subra, G. Mol. Biotechnol. 2006, 33, 239.

[1]	Deng Zhu, Zhi-Min Chen. Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3015-3032.
[2]	Xiaoyan Guo, Shuaijun Fang, Hongfei Qian, Gaofeng Feng. Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1703-1711.
[3]	Tian Xueqi, Zuo Minzan, Niu Pengbo, Wang Kaiya, Hu Xiaoyu. Research Advances of Host-Guest Supramolecular Self-Assemblies with Aggregration-Induced Emission Effect and Their Applications in Biomedical Field [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1823-1834.
[4]	Hu Zhixiong, Sun Dongdong, Han Xie, Liu Simin. Molecular Recognition of Cucurbit[10]uril toward Planar d⁸ and d¹⁰ Transition Metal Complexes [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1361-1366.
[5]	Xiao Tangxin, Zhou Ling, Wei Xiaoyan, Li Zhengyi, Sun Xiaoqiang. Supramolecular Copolymers Driven by Quadruple Hydrogen Bonding and Host-Guest Interactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 944-949.
[6]	Wang Shuqin, Huang Wanyun, Zhang Xiaorong, Zhang Xiaoting, Pan Chengxue. Synthesis and Bioactive Evaluation of Pyridazino-[6,1-b]quinazolinones Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 959-968.
[7]	Qi Lijie, Ding Yihan, Xiao Tangxin, Wu Haoran, Diao Kai, Bao Cheng, Shen Yong, Li Zhengyi, Sun Xiaoqiang, Wang Leyong. Supramolecular Self-Assembly of Dioxyphenylene Bridged Ureidopyrimidinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3847-3852.
[8]	Yang Yang, Li Ruomei, Wang Wei, Xu Zi-Wen, Xie Guanghui, Lu Zhengquan, Li Jingjing, Song Liping, Li Wei-Shi. Research Advances on the Mechanism of Polymer Solubilization and Selective Separation of Single-Wall Carbon Nanotubes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3249-3261.
[9]	Zhao Xinyu, Ding Yangyang, Lü Yingtao, Kang Congmin. Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds [J]. Chin. J. Org. Chem., 2019, 39(5): 1304-1315.
[10]	Zhang Shilong, Jiang Lasheng. Supramolecular Assembly Based on the Novel Sail-Boat-Shaped Self-Complexes [J]. Chin. J. Org. Chem., 2019, 39(3): 720-726.
[11]	Wu Mei, Huang Xinping, Zhang Haibing, Li Pengfei. Advances on Directing-Group Assisted meta-C-H Functionalization Catalyzed by Transition Metal [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3114-3131.
[12]	Li Zhenyi, Hou Nana, Shao Wei, Xiao Shoujun, Lin Chen, Wang Leyong. Host-Guest Interaction between Water-Soluble Pillar[6]arene and 1,1'-Disubstituted Ferrocene Derivatives [J]. Chin. J. Org. Chem., 2018, 38(8): 2002-2007.
[13]	Chen Lu, Bo Shuhui, He Yanling, Chen Zhuo, Liu Xinhou, Zhen Zhen. Organic Second-Order Nonlinear Optical Chromophores Modified by Isolation Groups [J]. Chin. J. Org. Chem., 2017, 37(9): 2263-2274.
[14]	Sun Guangjun, Nie Chengbin, Zhao Xin, Li Zhanting. Intramolecular C-H…O Hydrogen Bonding-Driven 1,2,3-Trazole Foldamers:Assessment of Intermolecular C-H…X^- (X=Cl, Br, I) and C-H…N Hydrogen Bonding [J]. Chin. J. Org. Chem., 2017, 37(7): 1757-1763.
[15]	Yi Junming, Chen Minghua, Xue Saifeng, Tao Zhu. Interaction and Supramocular Self-Assembly of Cucurbit[7]uril with 2,2'-(Heptane-1,7-diyl) Dibenzimidazolium Chloride [J]. Chin. J. Org. Chem., 2016, 36(3): 653-658.

寡肽转运蛋白特征基元III的固相合成与性质研究

Solid Phase Synthesis and Property of Signature Motif Ⅲ in Peptide Transporter

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments