4-羟基脯氨酸立体异构对α-芋螺毒素溶液构象的影响

doi:10.3866/PKU.WHXB201303111

Abstract

Abstract:

The hydroxylation of proline is a post-translational modification common in α-conotoxin and other conotoxin families. The 4-hydroxyl group of hydroxyproline adopts a trans conformation in native conotoxin, and this residue plays a key role in toxin structure and bioactivity. Little is known about the effects of the cis conformation of 4-hydroxyproline on conotoxin folding and bioactivity. The solution structures of three chemically modified α-conotoxin species containing cis- and trans-4-hydroxyproline were investigated using two-dimensional nuclear magnetic resonance (2D NMR). The selected α4/ 7-conopeptides included [γ15E]Sr1B, [O7O'/γ15E]Sr1B, and [O6O'/γ14E]Vc1A. The impact of modifying prolines cis/trans-4-hydroxyl group on the conopeptide structure was remarkable. Changing from trans- to cis-4-hydroxyproline led to notable solution conformational changes in α-conopeptide species. These included secondary structure elements, side chain orientations of key residues, and hydrogen-bonding properties. [O7O'/γ15E]Sr1B exhibited a twisted ω structure unlike that of typical α-conotoxin species. [O6O'/γ14E]Vc1A lost the turn structure around the N-/C-termini, which differed from that of Vc1.1. This study aids our understanding of the chemical modification of conotoxin, and is useful in elucidating the structure- bioactivity relationships of α-conotoxin species.

Key words: α-Conotoxin, Hydroxyproline, Stereochemistry, NMR, Solution conformation

MSC2000:

O641

Click here to download Supporting Info material in PDF type

ZHANG Bing-Bing, ZHAO Cong, WANG Xue-Song, HE Lei, DU Wei-Hong. Effects of 4-Hydroxyproline Stereochemistry on α-Conotoxin Solution Conformation[J].Acta Phys. -Chim. Sin., 2013, 29(05): 1080-1087.

References

(1) Terlau, H.; Olivera, B. M. Physiol. Rev. 2004, 84, 41. doi: 10.1152/physrev.00020.2003
(2) Halai, R.; Craik, D. J. Nat. Prod. Rep. 2009, 26, 526. doi: 10.1039/b819311h
(3) Azam, L.; McIntosh, J. M. Acta Pharmacol. Sin. 2009, 30, 771.doi: 10.1038/aps.2009.47
(4) Kaas, Q.; Yu, R.; Jin, A. H.; Dutertre, S.; Craik, D. J. NucleicAcids Res. 2012, 40, D325.
(5) Livett, B. G.; Sandall, D.W.; Keays, D.; Down, J.; Gayler, K.R.; Satkunanathan, N.; Khalil, Z. Toxicon 2006, 48, 810. doi: 10.1016/j.toxicon.2006.07.023
(6) Myers, R. A.; Cruz, L. J.; Rivier, J. E.; Olivera, B. M. Chem.Rev. 1993, 93, 1923. doi: 10.1021/cr00021a013
(7) Jin, A. H.; Daly, N. L.; Nevin, S. T.;Wang, C. A.; Dutertre, S.;Lewis, R. J.; Adams, D. J.; Craik, D. J.; Alewood, P. F. J. Med.Chem. 2008, 51, 5575. doi: 10.1021/jm800278k
(8) Buczek, O.; Bulaj, G.; Olivera, B. M. Cell Mol. Life Sci. 2005,62, 3067. doi: 10.1007/s00018-005-5283-0
(9) Craik, D. J.; Adams, D. J. ACS Chem. Biol. 2007, 2, 457. doi: 10.1021/cb700091j
(10) Armishaw, C. J. Toxins 2010, 2, 1471. doi: 10.3390/toxins2061471
(11) Clark, R. J.; Jensen, J.; Nevin, S. T.; Callaghan, B. P.; Adams, D.J.; Craik, D. J. Angew. Chem. Int. Edit. 2010, 49, 6545. doi: 10.1002/anie.201000620
(12) Muttenthaler, M.; Nevin, S. T.; Grishin, A. A.; Ngo, S. T.; Choy,P. T.; Daly, N. L.; Hu, S. H.; Armishaw, C. J.;Wang, C. I. A.;Lewis, R. J.; Martin, J. L.; Noakes, P. G.; Craik, D. J.; Adams,D. J.; Alewood, P. F. J. Am. Chem. Soc. 2010, 132, 3514. doi: 10.1021/ja910602h
(13) Lopez-Vera, E.;Walewska, A.; Skalicky, J. J.; Olivera, B. M.;Bulaj, G. Biochemistry 2008, 47, 1741. doi: 10.1021/bi701934m
(14) Xu, J.;Wang, Y. L.; Zhang, B. B.;Wang, B. H.; Du,W. H.Chem. Commun. 2010, 46, 5467. doi: 10.1039/c0cc00075b
(15) Calzolari, A.; Cicero, G.; Cavazzoni, C.; Di Felice, R.; Atellani,C. A.; Corni, S. J. Am. Chem. Soc. 2010, 132, 4790. doi: 10.1021/ja909823n
(16) Takeda, M.; Jee, J.; Ono, A. M.; Terauchi, T.; Kainosho, M.J. Am. Chem. Soc. 2011, 133, 17420. doi: 10.1021/ja206799v
(17) Denning, E. J.; MacKerell, A. D., Jr. J. Am. Chem. Soc. 2012,134, 2800. doi: 10.1021/ja211328g
(18) López-Vera, E.; Aguilar, M. B.; Schiavon, E.; Marinzi, C.; Ortiz,E.; Cassulini, R. R.; Batista, C. V. F.; Possani, L. D.; de laCotera, E. P. H.; Peri, F.; Becerril, B.;Wanke, E. FEBS J. 2007,274, 3972. doi: 10.1111/j.1742-4658.2007.05931.x
(19) Halai, R.; Clark, R. J.; Nevin, S. T.; Jensen, J. E.; Adams, D. J.;Craik, D. J. J. Biol. Chem. 2009, 284, 20275. doi: 10.1074/jbc.M109.015339
(20) Sandall, D.W.; Satkunanathan, N.; Keays, D. A.; Polidano, M.A.; Liping, X.; Pham, V.; Down, J. G.; Khalil, Z.; Livett, B. G.;Gayler, K. R. Biochemistry 2003, 42, 6904. doi: 10.1021/bi034043e
(21) Townsend, A.; Livett, B. G.; Bingham, J. P.; Truong, H. T.;Karas, J. A.; O'Donnell, P.;Williamson, N. A.; Purcell, A.W.;Scanlon, D. Inter. J. Pep. Res. Ther. 2009, 15, 195. doi: 10.1007/s10989-009-9173-4
(22) Armishaw, C.; Jensen, A. A.; Balle, T.; Clark, R. J.; Harpsøe, K.;Skonberg, C.; Liljefors, T.; Strømgaard, K. J. Biol. Chem. 2009,284, 9498. doi: 10.1074/jbc.M806136200
(23) Luo, S.; Nguyen, T. A.; Cartier, G. E.; Olivera, B. M.;Yoshikami, D.; McIntosh, J. M. Biochemistry 1999, 38, 14542.doi: 10.1021/bi991252j
(24) Park, K. H.; Suk, J. E.; Jacobsen, R.; Gray,W. R.; McIntosh, J.M.; Han, K. H. J. Biol. Chem. 2001, 276, 49028. doi: 10.1074/jbc.M107798200
(25) Clark, R. J.; Fischer, H.; Nevin, S. T.; Adams, D. J.; Craik, D. J.J. Biol. Chem. 2006, 281, 23254. doi: 10.1074/jbc.M604550200
(26) Nevin, S. T.; Clark, R. J.; Klimis, H.; Christie, M. J.; Craik, D.J.; Adams, D. J. Mol. Pharmacol. 2007, 72, 1406. doi: 10.1124/mol.107.040568
(27) Skjærbæk, N.; Nielsen, K. J.; Lewis, R. J.; Alewood, P. F.;Craik, D. J. J. Biol. Chem. 1997, 272, 2291. doi: 10.1074/jbc.272.4.2291
(28) Teichert, R.W.; Jimenez, E. C.; Olivera, B. M. Biochemistry2005, 44, 7897. doi: 10.1021/bi047274+
(29) Loughnan, M.; Nicke, A.; Jones, A.; Schroeder, C. I.; Nevin, S.T.; Adams, D. J.; Alewood, P. F.; Lewis, R. J. J. Biol. Chem.2006, 281, 24745. doi: 10.1074/jbc.M603703200
(30) Jakubowski, J. A.; Keays, D. A.; Kelley,W. P.; Sandall, D.W.;Bingham, J. P.; Livett, B. G.; Gayler, K. R.; Sweedler, J. V.J. Mass Spectrom. 2004, 39, 548.
(31) Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 65, 355.
(32) Jeener, J.; Meier, B. H.; Bachmann, P.; Ernst, R. R. J. Chem.Phys. 1979, 71, 4546. doi: 10.1063/1.438208
(33) Goddard, T. D.; Kneller, D. G. Sparky 3; University ofCalifornia, San Francisco, CA, 2007.
(34) Güntert, P.; Mumenthaler, C.; Wüthrich, K. J. Mol. Biol. 1997,273, 283. doi: 10.1006/jmbi.1997.1284
(35) Koradi, R.; Billeter, M.; Wüthrich, K. J. Mol. Graph. 1996, 14,51. doi: 10.1016/0263-7855(96)00009-4
(36) Wüthrich, K. NMR of Proteins and Nucleic Acids;Wiley: NewYork, 1986.
(37) Huang, F. J.; Du,W. H.;Wang, B. B. Acta Phys.-Chim. Sin.2008, 24, 1558. [黄飞娟, 杜为红, 王保怀. 物理化学学报,2008, 24, 1558.] doi: 10.1016/S1872-1508(08)60064-9
(38) Zhang, B. B.; Huang, F. J.; Du,W. H. Amino Acids 2012, 43,389. doi: 10.1007/s00726-011-1093-x
(39) Chi, C.W. Chin. Sci. Bull. 2009, 54, 2734. [戚正武. 科学通报, 2009, 54, 2734.] doi: 10.1360/972009-1582
(40) Dutertre, S.; Nicke, A.; Lewis, R. J. J. Biol. Chem. 2005, 280,30460. doi: 10.1074/jbc.M504229200
(41) Ulens, C.; Hogg, R. C.; Celie, P. H.; Bertrand, D.; Tsetlin, V.;Smit, A. B.; Sixma, T. K. Proc. Natl. Acad. Sci. U. S. A. 2006,103, 3615. doi: 10.1073/pnas.0507889103
(42) Quiram, P. A.; Sine, S. M. J. Biol. Chem. 1998, 273, 11007. doi: 10.1074/jbc.273.18.11007
(43) Yu, R.; Craik, D. J.; Kaas, Q. PLoS Comput. Biol. 2011, 7,e1002011.

[1]	Chao Li, Ming Shen, Bingwen Hu. Solid-State NMR and EPR Methods for Metal Ion Battery Research [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1902019-0.
[2]	Shihan Li,Zhenchao Zhao,Shikun Li,Youdong Xing,Weiping Zhang. Aluminum Distribution and Brønsted Acidity of Al-Rich SSZ-13 Zeolite: A Combined DFT Calculation and Solid-State NMR Study [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1903021-0.
[3]	Feng Shi,Lili Hu,Jinjun Ren,Qiuhong Yang. Structural Investigation of Alkaline-Earth Phosphosilicate Glasses Containing Six-Coordinated Silicon by Solid-State NMR [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1902018-0.
[4]	Yi Ji, Lixin Liang, Changmiao Guo, Xinhe Bao, Tatyana Polenova, Guangjin Hou. Zero-Quantum Homonuclear Recoupling Symmetry Sequences in Solid-State Fast MAS NMR Spectroscopy [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1905029-0.
[5]	Xiaolong Liu, Qiang Wang, Chao Wang, Jun Xu, Feng Deng. Hydrogen-Bond Induced Crystallization of Silicalite-1 Zeolite as Revealed by Solid-State NMR Spectroscopy [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1905035-0.
[6]	Jing Deng,Tao Ma,Ziwei Chang,Weijing Zhao,Jun Yang. Determination of Three-Dimensional Structures of Protein Assemblies via Solid-State NMR [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1905019-0.
[7]	Yuhong Li,Xin-Ping Wu,Cong Liu,Meng Wang,Benteng Song,Guiyun Yu,Gang Yang,Wenhua Hou,Xue-Qing Gong,Luming Peng. NMR and EPR Studies of Partially Reduced TiO₂ [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1905021-0.
[8]	Yongchao Shi, Mingxue Tang. NMR/EPR Investigation of Rechargeable Batteries [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1905004-0.
[9]	Fenfen Wang, Peng Wang, Hongyao Niu, Yingfeng Yu, Pingchuan Sun. Solid-State NMR Studies on Hydrogen Bonding Interactions and Structural Evolution in PAA/PEO Blends [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1912016-0.
[10]	Yingxiong Wang, Manli Deng, Yongqiang Tang, Yuchun Han, Xu Huang, Yanbo Hou, Yilin Wang. Aggregation of Biodegradable Cationic Gemini Surfactants with Amide or Ester Groups [J]. Acta Physico-Chimica Sinica, 2020, 36(10): 1909046-0.
[11]	Zhimin XUE,Chuanyu YAN,Xinhui ZHAO,Dongkun YU,Tiancheng MU. How Hofmeister Ions Change the Local Environment around Thermoresponsive Polymers in Aqueous Solutions: an NMR Study [J]. Acta Phys. -Chim. Sin., 2019, 35(1): 49-57.
[12]	Shen-Hui LI,Jing LI,An-Min ZHENG,Feng DENG. Solid-State NMR Characterization of the Structure and Catalytic Reaction Mechanism of Solid Acid Catalysts [J]. Acta Phys. -Chim. Sin., 2017, 33(2): 270-282.
[13]	AL-SEHEMI Abdullah G., Al-AMRI Reem S. Abdulaziz, IRFAN Ahmad. Characterization and Density Functional Theory Investigations of 3-Monoacylaminoquinazolinone Derivatives [J]. Acta Phys. -Chim. Sin., 2013, 29(01): 55-63.
[14]	HE Rui, JIAO Yan-Hua, LIANG Yuan-Yuan, CHEN Can-Yu. Accurate Predictions of the NMR Parameters in Organic and Biological Crystallines [J]. Acta Phys. -Chim. Sin., 2011, 27(09): 2051-2058.
[15]	ZHANG Xiao-Hong, GUO Hong-Rui, JIAO Zhi, YAN Wei-Wei, RUAN Wen-Juan, ZHU Zhi-Ang. Weak Interactions in Asymmetric Porphyrin Systems [J]. Acta Phys. -Chim. Sin., 2011, 27(04): 774-780.

Effects of 4-Hydroxyproline Stereochemistry on α-Conotoxin Solution Conformation

PDF (PC)

Like

Knowledge

Abstract

Supporting Info

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 0