α,β-Dehydroamino acids in naturally occurring peptides.

α,β-Dehydroamino acids in naturally occurring peptides.
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DOI:
10.1007/s00726-014-1846-4
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发表时间:
2015-01
期刊:
影响因子:
3.5
通讯作者:
Siodlak, Dawid
Siodlak, Dawid
中科院分区:
生物学3区
文献类型:
--
作者:
Siodlak, Dawid

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α,β-脱氢氨基酸是天然存在的非编码氨基酸,主要存在于肽中。本文综述了α,β-脱氢氨基酸的种类、脱氢肽的结构、来源及生物活性。脱氢肽主要从细菌中分离,很少从真菌、海洋无脊椎动物甚至高等植物中分离。它们主要具有抗菌、抗真菌、抗肿瘤和植物毒性活性。超过60种不同的结构被分类,通常涵盖广泛的肽家族。含有α,β-脱氢氨基酸残基的37个不同结构单元包括各种侧链、Z和E异构体以及主要修饰:肽键的甲基化以及酯基和杂环的引入。收集的数据显示了结构与生物活性之间的关系。这使得化合物的活性,这是没有研究在这个领域,但属于一个更大的肽家族被预测。一些实例表明,α,β-脱氢氨基酸残基的几何异构体的类型对于生物活性可能是重要的,甚至是至关重要的。本文的在线版本(doi:10.1007/s 00726 -014-1846-4)包含补充材料,可供授权用户使用。
α,β-Dehydroamino acids are naturally occurring non-coded amino acids, found primarily in peptides. The review focuses on the type of α,β-dehydroamino acids, the structure of dehydropeptides, the source of their origin and bioactivity. Dehydropeptides are isolated primarily from bacteria and less often from fungi, marine invertebrates or even higher plants. They reveal mainly antibiotic, antifungal, antitumour, and phytotoxic activity. More than 60 different structures were classified, which often cover broad families of peptides. 37 different structural units containing the α,β-dehydroamino acid residues were shown including various side chains, Z and E isomers, and main modifications: methylation of peptide bond as well as the introduction of ester group and heterocycle ring. The collected data show the relation between the structure and bioactivity. This allows the activity of compounds, which were not studied in this field, but which belong to a larger peptide family to be predicted. A few examples show that the type of the geometrical isomer of the α,β-dehydroamino acid residue can be important or even crucial for biological activity. The online version of this article (doi:10.1007/s00726-014-1846-4) contains supplementary material, which is available to authorized users.
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