Citation: 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 Physico-Chimica Sinica, ;2013, 29(05): 1080-1087. doi: 10.3866/PKU.WHXB201303111 shu

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

1.
Department of Chemistry, Renmin University of China, Beijing 100872

Received Date: 8 January 2013
Available Online: 11 March 2013
Fund Project: 国家重点基础研究发展规划项目(973) (2011CB808503) (973) (2011CB808503) 教育部科技重点项目(108121) (108121)北京化工大学化工资源有效利用国家重点实验室开放课题(CRF-2012-C-102)资助 (CRF-2012-C-102)

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.
- α-Conotoxin,
- Hydroxyproline,
- Stereochemistry,
- NMR,
- Solution conformation
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