Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides

Reddy Kishorkumar M.; Mugesh Govindasamy

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Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides

机译：脱氢碱作为合成含硒盐肽肽的构建块

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Selenocysteine (Sec), the 21(st) proteinogenic amino acid, is inserted co-translationally into number of natural proteins. It is coded by a dual function stop codon UGA (opal). It is a redox active amino acid found at the active sites of several enzymes that are involved in oxidation-reduction reactions. These enzymes include the three major mammalian selenoproteins glutathione peroxidase (GPx), thioredoxin reductase (TrxR), and iodothyronine deiodinase (Dio). Although Sec is structurally similar to its sulfur analogue cysteine (Cys), the lower pK(a) of the selenol group in Sec as compared to that of Cys and the interesting redox properties of the selenium atom in peptides and proteins play crucial roles in redox catalysis. However, the chemical synthesis of Sec-containing peptides has been a difficult task. In this paper, we report on a new method for the synthesis of Sec and Sec-containing peptides using dehydroalanine (Dha) as a building block.

机译：Selenocysteine（SEC），21（ST）蛋白原氨基酸，共同翻译成天然蛋白的数量。它由双功能停止密码子UGA（opal）编码。它是在几种酶的活性位点发现的氧化还原活性氨基酸，其参与氧化还原反应。这些酶包括三个主要的哺乳动物硒蛋白谷胱甘肽过氧化物酶（GPX），硫氧化辛还原酶（TRXR）和碘罗酮脱碘酶（DIO）。虽然SEC在结构上类似于其硫类似物半胱氨酸（Cys），但与Cys的亚苯酚基团的下部PK（A）相比，肽和蛋白质中硒原子的有趣氧化还原性能在氧化还原中起重要作用催化。然而，含第二肽的化学合成是一项艰巨的任务。在本文中，我们报告了使用脱氢碱（DHA）作为构建块合成含SEC和含第二次肽的新方法。

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《RSC Advances》 |2019年第1期|共10页
作者
Reddy Kishorkumar M.; Mugesh Govindasamy;
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Indian Inst Sci Dept Inorgan &

Phys Chem Bangalore 560012 Karnataka India;

Indian Inst Sci Dept Inorgan &

Phys Chem Bangalore 560012 Karnataka India;

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正文语种 eng
中图分类化学;
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1. Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides [J] . Reddy Kishorkumar M., Mugesh Govindasamy RSC Advances . 2019,第1期

机译：脱氢碱作为合成含硒盐肽肽的构建块
2. Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides [J] . Kishorkumar?M. Reddy, Govindasamy Mugesh RSC Advances . 2019,第1期

机译：脱氢丙氨酸作为合成含硒代半胱氨酸肽的基础材料的应用
3. Easy preparation of dehydroalanine building blocks equipped with oxazolidin-2-one chiral auxiliaries, and applications to the stereoselective synthesis of substituted tryptophans [J] . Rossella De Marco, Lorenzo Cavina, Arianna Greco Amino acids . 2014,第12期

机译：易于制备配有恶唑烷-2-酮手性助剂的脱氢丙氨酸结构单元，并应用于取代色氨酸的立体选择性合成
4. SYNTHESIS OF BUILDING BLOCKS FOR PEPTIDE SYNTHESIS BY USING 4-(4,6-DIMETHOXY-1,3,5TRIAZIN-2-YL)-4-METHYL-MORPHOLINIUM TOLUENE-4-SULFONATE [C] . Beata Kolesinska, Justyna Kolesinska, Anna Frymarkiewicz the European Peptide Symposium . 2007

机译：用4-（4,6-二甲氧基 - 1,3,5三氮辛-2-基）-4-甲基 - 吗啉甲苯-4-磺酸盐合成肽合成的构建块
5. The synthesis and characterization of novel biomaterials from natural building blocks: Biomaterials research: Past, present, and future directions, and, Saccharide-derived polymers as protein resistant biomaterials, and, Saccharide-peptide copolymers for gene delivery applications, and, Saccharide-peptide copolymer hydrogels for extracellular scaffold design. [D] . Metzke, Mark Adam. 2006

机译：从天然构件中合成和表征新型生物材料：生物材料研究：过去，现在和未来的方向，以及，糖衍生的聚合物作为抗蛋白质生物材料，以及用于基因传递应用的糖肽共聚物，以及糖肽共聚物水凝胶用于细胞外支架设计。
6. Self-Assembling Peptide-Based Building Blocks in Medical Applications [O] . Handan Acar, Samanvaya Srivastava, Eun Ji Chung, -1

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7. Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides [O] . Kishorkumar M. Reddy, Govindasamy Mugesh 2019

机译：脱氢碱作为合成含硒盐肽肽的构建块

Application of dehydroalanine as a building block for the synthesis of selenocysteine-containing peptides

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