Effect of Michael adduction on peptide preservation in natural waters.

Effect of Michael adduction on peptide preservation in natural waters.
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迈克尔加成对天然水中肽保存的影响。

DOI:
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发表时间:
2014
期刊:
Environmental Science: Processes & Impacts
影响因子:
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通讯作者:
P. Hatcher
P. Hatcher
中科院分区:
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文献类型:
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作者:
G. A. McKee;M. E. Kobiela;P. Hatcher

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肽与天然沃茨中已经存在的化学物质(如多环芳烃)的反应是一种已被建议长期保存肽的方法。在这项研究中,我们测试是否四肽与模型醌的反应可以帮助稳定的肽在一个污染的河流系统,伊丽莎白河在美国弗吉尼亚州。我们发现肽和其醌加合物之间的速率常数几乎没有差异(例如,对于AVFA和其各自的加合物,每天6.62对6.86)。然而,当监测从天然水中去除加合物时,我们发现了两种新的化合物,它们是由于其分解而形成的。使用串联质谱,我们确定了这些新化合物形成的潜在结构和机制。这些新化合物比它们的母体肽-醌加合物更难溶,因为它们在溶液中的停留时间长3-10倍。基于我们的研究结果,我们假设,与醌的肽的反应可以帮助保存部分的原始肽后,最初的加合物的重排,可能解释为什么看似不稳定的肽在大多数天然沃茨中观察到。
The reaction of peptides with chemicals already present in natural waters (such as polycyclic aromatic hydrocarbons) is one method that has been suggested to preserve peptides for the longer term. In this study we test whether the reaction of tetrapeptides with a model quinone can help stabilise the peptide in one polluted riverine system, Elizabeth River in Virginia, USA. We found that there is almost no difference in rate constants between the peptide and its quinone adduct (e.g. 6.62 versus 6.86 per day for AVFA and its respective adduct). However, when monitoring the removal of the adduct from natural water, we identified two new compounds that are formed as a result of its decomposition. Using tandem mass spectrometry we identified potential structures and mechanisms for the formation of these new compounds. These new compounds are more recalcitrant than their parent peptide-quinone adduct, since they remain in solution for 3-10 times longer. Based on our findings we postulate that the reaction of peptides with quinones can help preserve sections of the original peptide following an initial rearrangement of the original adduct, potentially explaining why seemingly labile peptides are observed in most natural waters.
DOI: 10.1021/tx9902082
发表时间: 2000-03-01
影响因子: 4.1
作者:
Bolton, JL;Trush, MA;Monks, TJ
通讯作者: Monks, TJ
DOI: 10.1016/j.gca.2012.01.002
发表时间: 2012-04-15
影响因子: 5
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