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Insight into the Structure of Victorin, the Host-Selective Toxin from the Oat Pathogen Cochliobolus victoriae. Studies of the Unique Dehydroamino Acid β-Chlorodehydroalanine
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-07-24 , DOI: 10.1021/acs.jafc.3c01387 Karolina Banaś 1 , Paweł Lenartowicz 1 , Monika Staś 1 , Błażej Dziuk 2, 3 , Dawid Siodłak 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-07-24 , DOI: 10.1021/acs.jafc.3c01387 Karolina Banaś 1 , Paweł Lenartowicz 1 , Monika Staś 1 , Błażej Dziuk 2, 3 , Dawid Siodłak 1
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Victorins, a family of peptide toxins, produced by the fungal pathogen Cochliobolus victoriae and responsible for disease of some oat varieties, contain a β-chlorodehydroalanine residue, ΔAla(βCl). To determine the conformational properties of this unique dehydroamino acid, a series of model compounds was studied using X-ray, NMR, and FT-IR methods, supported by theoretical calculations. The ΔAla(βCl) geometrical isomers differ in conformational profile. The isomer Z prefers the helical conformation α (φ, ψ = −61°, −24°), PPII type conformation β (φ, ψ = −47°, 136°), and semiextended conformation β2 (φ, ψ = −116°, 9°) in weakly and more polar solutions. The isomer E prefers mainly the extended conformation C5 (φ, ψ = −177°, 160°), but with an increase of the environment polarity also conformations β (φ, ψ = −44°, 132°) and α (φ, ψ = −53°, −39°). In the most stable conformations the N-H···Cl hydrogen bond (5γ) occurs, created between the chlorine atom of the side chain and the N-H donor of the flanking amide group. The method of synthesis of the β-chlorodehydroalanine residue is proposed, by chlorination of dehydroalanine and then the photoisomerization from the isomer Z to E. The presented results indicate that the assignment of the geometrical isomer of the ΔAla(βCl) residue in naturally occurring victorins still remains an open question, despite being crucial for biological activity.
中文翻译:
深入了解 Victorin 的结构,Victorin 是来自燕麦病原体 Cochliobolus victoriae 的宿主选择性毒素。独特脱氢氨基酸β-氯脱氢丙氨酸的研究
Victorins 是一种肽毒素家族,由真菌病原体胜利旋孢菌 ( Cochliobolus victoriae)产生,导致某些燕麦品种的疾病,含有 β-氯脱氢丙氨酸残基 ΔAla(βCl)。为了确定这种独特脱氢氨基酸的构象特性,在理论计算的支持下,使用 X 射线、NMR 和 FT-IR 方法研究了一系列模型化合物。ΔAla(βCl) 几何异构体的构象特征不同。异构体Z更喜欢螺旋构象α(φ,ψ=-61°,-24°),PPII型构象β(φ,ψ=-47°,136°)和半伸展构象β2(φ,ψ=-116) °,9°)在弱极性和极性较大的溶液中。异构体E主要倾向于扩展构象 C5 (φ, ψ = -177°, 160°),但随着环境极性的增加,构象 β (φ, ψ = -44°, 132°) 和 α (φ, ψ = -44°, 132°) ψ = −53°, −39°)。在最稳定的构象中,NH·Cl 氢键 (5 γ ) 出现在侧链的氯原子和侧翼酰胺基团的 NH 供体之间。提出了β-氯代脱氢丙氨酸残基的合成方法,先将脱氢丙氨酸氯化,然后光异构化,从异构体Z变为E。所提出的结果表明,天然存在的victorins中ΔAla(βCl)残基的几何异构体的归属仍然是一个悬而未决的问题,尽管对于生物活性至关重要。
更新日期:2023-07-24
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
深入了解 Victorin 的结构,Victorin 是来自燕麦病原体 Cochliobolus victoriae 的宿主选择性毒素。独特脱氢氨基酸β-氯脱氢丙氨酸的研究
Victorins 是一种肽毒素家族,由真菌病原体胜利旋孢菌 ( Cochliobolus victoriae)产生,导致某些燕麦品种的疾病,含有 β-氯脱氢丙氨酸残基 ΔAla(βCl)。为了确定这种独特脱氢氨基酸的构象特性,在理论计算的支持下,使用 X 射线、NMR 和 FT-IR 方法研究了一系列模型化合物。ΔAla(βCl) 几何异构体的构象特征不同。异构体Z更喜欢螺旋构象α(φ,ψ=-61°,-24°),PPII型构象β(φ,ψ=-47°,136°)和半伸展构象β2(φ,ψ=-116) °,9°)在弱极性和极性较大的溶液中。异构体E主要倾向于扩展构象 C5 (φ, ψ = -177°, 160°),但随着环境极性的增加,构象 β (φ, ψ = -44°, 132°) 和 α (φ, ψ = -44°, 132°) ψ = −53°, −39°)。在最稳定的构象中,NH·Cl 氢键 (5 γ ) 出现在侧链的氯原子和侧翼酰胺基团的 NH 供体之间。提出了β-氯代脱氢丙氨酸残基的合成方法,先将脱氢丙氨酸氯化,然后光异构化,从异构体Z变为E。所提出的结果表明,天然存在的victorins中ΔAla(βCl)残基的几何异构体的归属仍然是一个悬而未决的问题,尽管对于生物活性至关重要。