The Uniqueness of Tryptophan in Biology: Properties, Metabolism, Interactions and Localization in Proteins.

The Uniqueness of Tryptophan in Biology: Properties, Metabolism, Interactions and Localization in Proteins.
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DOI:
10.3390/ijms21228776
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发表时间:
2020-11-20
影响因子:
5.6
通讯作者:
Barik S
Barik S
中科院分区:
生物学2区
文献类型:
--
作者:
Barik S

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色氨酸(Trp)在生物学中占有独特的地位,原因有很多。它是翻译工具箱中所有20种氨基酸中最大的一种。其侧链是吲哚,其是具有双核环结构的芳香族,而Phe、Tyr和His的侧链是单环芳香族。部分由于这些复杂的结构特征,Trp的生物合成途径是所有氨基酸中最复杂和最耗能的。色氨酸是动物饮食中必不可少的,也是细胞中含量最少的氨基酸,也是蛋白质组中最稀有的氨基酸之一。在大多数真核生物中,Trp是除了Met之外的唯一氨基酸,Met由单个密码子编码,即UGG。由于大的疏水性π电子表面积,其芳香族侧链与蛋白质中的多个其他侧链相互作用,适合其在蛋白质结构中的战略位置。最后,几种色氨酸衍生物,即蒽醌、奥昔曲普坦、血清素、褪黑激素和羟色胺,具有专门的功能。总的来说,色氨酸是细胞中稀缺而珍贵的氨基酸,因此自然界吝啬地使用它,用于多种但有选择性的功能。在这里,色氨酸的独特性的各个方面提出了在分子方面。
Tryptophan (Trp) holds a unique place in biology for a multitude of reasons. It is the largest of all twenty amino acids in the translational toolbox. Its side chain is indole, which is aromatic with a binuclear ring structure, whereas those of Phe, Tyr, and His are single-ring aromatics. In part due to these elaborate structural features, the biosynthetic pathway of Trp is the most complex and the most energy-consuming among all amino acids. Essential in the animal diet, Trp is also the least abundant amino acid in the cell, and one of the rarest in the proteome. In most eukaryotes, Trp is the only amino acid besides Met, which is coded for by a single codon, namely UGG. Due to the large and hydrophobic π-electron surface area, its aromatic side chain interacts with multiple other side chains in the protein, befitting its strategic locations in the protein structure. Finally, several Trp derivatives, namely tryptophylquinone, oxitriptan, serotonin, melatonin, and tryptophol, have specialized functions. Overall, Trp is a scarce and precious amino acid in the cell, such that nature uses it parsimoniously, for multiple but selective functions. Here, the various aspects of the uniqueness of Trp are presented in molecular terms.
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