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Impact of D 2 O on peptidization of l -hydroxyproline
Reaction Kinetics, Mechanisms and Catalysis ( IF 1.8 ) Pub Date : 2020-01-01 , DOI: 10.1007/s11144-019-01711-9
Agnieszka Fulczyk , Eliza Łata , Ewa Talik , Teresa Kowalska , Mieczysław Sajewicz

This is our fourth consecutive study carried out in an order to collect experimental evidence regarding the impact of heavy water (D2O) on the spontaneous oscillatory peptidization of proteinogenic α-amino acids and this time its subject matter is l-hydroxyproline (l-Hyp). Our three earlier studies have been focused on the two sulfur-containing α-amino acids, i.e., l-cysteine (l-Cys) and l-methionine (l-Met), and on one structurally related α-amino acid, i.e., l-proline (l-Pro). It seemed interesting to assess the effect induced by D2O on l-Hyp and to compare it with the effects valid for l-Cys, l-Met, and l-Pro. As analytical techniques, we used high-performance liquid chromatography with the evaporative light-scattering detection (HPLC-ELSD), mass spectrometry (MS), and scanning electron microscopy (SEM). The obtained results make it clear that the impact of heavy water on dynamics of spontaneous peptidization of l-Hyp differs from that exerted on three other α-amino acids discussed (although in all four cases, heavy water significantly hampers spontaneous oscillatory peptidization). With l-Hyp, an increasing proportion of D2O in the reaction mixture results in decreasing yields of both, the soluble lower molecular weight peptides and the insoluble higher molecular weight peptides. With the two sulfur-containing compounds (l-Cys and l-Met), an increasing proportion of D2O in the reaction mixture resulted in growing yields of the soluble lower molecular weight peptides at an expense of decreasing yields of the insoluble higher molecular weight peptides. With l-Pro, still different pattern was observed, namely that the hampering effect of D2O on peptidization was not monotonously dependent on the concentration of D2O in the system, but it was the strongest pronounced for 10% (v/v) D2O in the employed binary methanol–water solvent (with the investigated proportions of D2O in this solvent changing from 0 to 30%). We hope that firm quantitative results presented in this study (and also in the three earlier studies from this cycle) can prove an inspiration for future researchers interested in getting a deeper insight into the role of D2O in life processes, and more specifically in the kinetic and mechanistic aspects thereof. Perhaps it might be noteworthy to add that out of four α-amino acids investigated so far, which can be divided into two groups of the endogenous (l-Cys and l-Pro) and exogenous (l-Met and l-Hyp) species, the endogenous species undergo spontaneous peptidization following the circadian rhythm, whereas the exogenous ones (including l-Hyp) do not.

中文翻译:

D 2 O对1-羟脯氨酸肽化的影响

这是我们连续第四次研究中的顺序进行收集实验证据有关的重水的影响(d 2 O)对含有蛋白α氨基酸自发振荡肽化,这个时候它的主题是羟基脯氨酸(- Hyp)。我们的三项早期研究集中在两种含硫的α-氨基酸,即l-半胱氨酸(l -Cys)和l-蛋氨酸(l -Met),以及一种与结构相关的α-氨基酸,即l-脯氨酸(l -Pro)。评估D 2 O对l的影响似乎很有趣。-Hyp,并将其与对l -Cys,l -Met和l -Pro有效的效果进行比较。作为分析技术,我们使用了具有蒸发光散射检测(HPLC-ELSD),质谱(MS)和扫描电子显微镜(SEM)的高效液相色谱仪。所获得的结果清楚地表明,重水对1- Hyp自发肽化动力学的影响与所讨论的其他三种α-氨基酸所施加的影响不同(尽管在所有四种情况下,重水均会严重阻碍自发振荡肽化)。随着l -Hyp,D 2的比例增加反应混合物中的O导致可溶的较低分子量的肽和不可溶的较高分子量的肽的产率降低。使用两种含硫化合物(1 - Cys和1- Met),反应混合物中D 2 O比例的增加导致可溶性低分子量肽的产率提高,但以降低不溶性较高分子量的产率为代价重肽。使用l -Pro时,仍然观察到不同的模式,即D 2 O对肽化的阻碍作用并非单调依赖于系统中D 2 O的浓度,但在10%(v / v)时最明显。 D 2所用的二元甲醇-水溶剂中的O(研究的D 2 O在该溶剂中的比例从0%更改为30%)。我们希望本研究(以及该周期的三项较早研究)中提出的可靠的定量结果能够为未来的研究人员提供灵感,这些研究人员希望对D 2 O在生命过程中的作用有更深入的了解,更具体地说是在生命过程中。其动力学和机械方面。也许值得一提的是,到目前为止已研究的四种α-氨基酸可分为内源性(I- Cys和I- Pro)和外源性(I- Met和I-I)两组。-Hyp)物种,内生物种会按照昼夜节律自发进行肽化作用,而外源物种(包括1- Hyp)则不会。
更新日期:2020-01-01
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