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

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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.

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

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