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Tetrahydrofuranyl and Tetrahydropyranyl Protection of Amino Acid Side-Chains Enables Synthesis of a Hydroxamate-Containing Aminoacylated tRNA

机译：氨基酸侧链的四氢呋喃基和四氢吡喃基保护能够合成含异羟肟酸酯的氨基酰化tRNA。

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The ability to specifically engineer metal binding sites into target proteins has far-reaching consequences ranging from the development of new biocatalysts and imaging reagents to the production of proteins with increased stability. We report the efficient tRNA-mediated incorporation of the hydroxamate containing amino acid, N^ε-acetyl-N^ε-hydroxy->l-lysine, into a transcription factor (TFIIIA). Because this amino acid is compact, hydrophilic, and uncharged at physiological pH, it should have little or no effect on protein folding or solubility. The N^ε-hydroxy group of the hydroxamate is refractory to photodeprotection and required the identification of reagents for O-protection that are compatible with the synthesis of acylated tRNA. Tetrahydrofuranyl and tetrahydropyranyl O-protecting groups can be removed using mild acid conditions and allowed for an orthogonal protection strategy in which deprotection of the amino acid side chain precedes ligation of an acylated dinucleotide to a truncated suppressor tRNA. These protecting groups will provide a valuable alternative for O-protection, especially in cases where photodeprotection cannot be used.

机译：特异地将金属结合位点工程化为目标蛋白质的能力具有深远的影响，从开发新的生物催化剂和显像剂到生产具有更高稳定性的蛋白质。我们报告了高效的tRNA介导的含有异羟肟酸酯的氨基酸N ^{ε-乙酰基-N ^{ε-羟基-> l -赖氨酸的掺入，成转录因子（TFIIIA）。由于该氨基酸是致密的，亲水的，并且在生理pH下不带电荷，因此它对蛋白质折叠或溶解度的影响很小或没有影响。异羟肟酸酯的N ^{ε-羟基对光脱保护是难处理的，需要鉴定与酰化tRNA合成兼容的O-保护试剂。可以使用弱酸条件除去四氢呋喃基和四氢吡喃基的O保护基，并采用正交保护策略，在该策略中，氨基酸侧链的脱保护先于酰化的二核苷酸与截短的抑制子tRNA连接。这些保护基将为O保护提供有价值的替代方法，尤其是在不能使用光脱保护的情况下。}}}

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期刊名称 other
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Lester J. Lambert; Marvin J. Miller; Paul W. Huber;
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年(卷),期 -1(13),8
年度 -1
页码 2341–2349
总页数 22
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专利

1. Tetrahydrofuranyl and tetrahydropyranyl protection of amino acid side-chains enables synthesis of a hydroxamate-containing aminoacylated tRNA [J] . Lester J. Lambert, Marvin J. Miller, Paul W. Huber Organic & biomolecular chemistry . 2015,第8期

机译：氨基酸侧链的四氢呋喃基和四氢吡喃基保护能够合成含异羟肟酸酯的氨基酰化tRNA
2. Contribution of the Esterified Amino Acid to the Binding of Aminoacylated tRNAs to the Ribosomal P- and A-Sites [J] . Richard P.Fahlman, Olke C.Uhlenbeck Biochemistry . 2004,第23期

机译：酯化氨基酸对氨基酰化tRNA与核糖体P位和A位点结合的贡献
3. Efficient tetrahydropyranyl and tetrahydrofuranyl protection/deprotection of alcohols and phenols with Al(OTf)_3 as catalyst [J] . Williams D.B.G., Simelane S.B., Lawton M., Tetrahedron . 2010,第25期

机译：Al（OTf）_3催化的醇和酚类四氢吡喃基和四氢呋喃基保护/脱保护
4. Mimicry of the backbone and side-chain geometry of peptide turns:synthesis of novel 4-substituted indolizindin-9-one amino acids [C] . Jerome Cluzeau, William D.Lubell the International Peptide Symposium . 2001

机译：肽的骨干和侧链几何形状的模拟性转弯：新型4-取代的吲哚嗪-9-on氨基酸的合成
5. Structure-based design of mutant proteins: I. Molecular docking studies of amino acid binding to wild-type aminoacyl-tRNA synthetases. II. Structure-based design of mutant aminoacyl-tRNA synthetases for non-natural amino acid incorporation. [D] . Zhang, Deqiang. 2003

机译：基于结构的突变蛋白设计：I.氨基酸与野生型氨酰基tRNA合成酶结合的分子对接研究。二。非天然氨基酸掺入的突变型氨酰基-tRNA合成酶的基于结构的设计。
6. Tetrahydropyranyl: A Non‐aromatic Mild‐Acid‐Labile Group for Hydroxyl Protection in Solid‐Phase Peptide Synthesis [O] . Dr. Anamika Sharma, Dr. Iván Ramos‐Tomillero, Prof. Ayman El‐Faham, 2017

机译：四氢吡喃基：固相肽合成中保护羟基的非芳香族弱酸不稳定基团
7. Bismuth(III) bromide in organic synthesis. A catalytic method for the allylation of tetrahydrofuranyl and tetrahydropyranyl ethers [O] . Mohan, Ram, Krabbe, Scott, Angeles, Veronica 2010

机译：有机合成中的溴化铋（III）。四氢呋喃基醚和四氢吡喃基醚的烯丙基化的催化方法

Tetrahydrofuranyl and Tetrahydropyranyl Protection of Amino Acid Side-Chains Enables Synthesis of a Hydroxamate-Containing Aminoacylated tRNA

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