将4-氟组氨酸基因掺入肽中可实现选择性亲和纯化。
Genetic incorporation of 4-fluorohistidine into peptides enables selective affinity purification.
作者信息
Ring Christine M, Iqbal Emil S, Hacker David E, Hartman Matthew C T, Cropp T Ashton
机构信息
Virginia Commonwealth University, Department of Chemistry, 1001 West Main Street, Richmond, Virginia 23284-2006, USA.
出版信息
Org Biomol Chem. 2017 May 31;15(21):4536-4539. doi: 10.1039/c7ob00844a.
Abstract
Due to the lowered pK of 4-fluorohistidine relative to histidine, peptides and proteins containing this amino acid are potentially endowed with novel properties. We report here the optimized synthesis of 4-fluorohistidine and show that it can efficiently replace histidine in in vitro translation reactions. Moreover, peptides containing 6×-fluorohistidine tags are able to be selectively captured and eluted from nickel resin in the presence of his-tagged protein mixtures.
摘要
由于4-氟组氨酸的pK相对于组氨酸降低，含有这种氨基酸的肽和蛋白质可能具有新的特性。我们在此报告4-氟组氨酸的优化合成，并表明它可以在体外翻译反应中有效替代组氨酸。此外，在存在组氨酸标签蛋白混合物的情况下，含有6×-氟组氨酸标签的肽能够从镍树脂中被选择性捕获和洗脱。
相似文献
1
Genetic incorporation of 4-fluorohistidine into peptides enables selective affinity purification.将4-氟组氨酸基因掺入肽中可实现选择性亲和纯化。
Org Biomol Chem. 2017 May 31;15(21):4536-4539. doi: 10.1039/c7ob00844a.
2
The Biophysical Probes 2-fluorohistidine and 4-fluorohistidine: Spectroscopic Signatures and Molecular Properties.2-氟组氨酸和 4-氟组氨酸的生物物理探针：光谱特征和分子性质。
Sci Rep. 2017 Feb 15;7:42651. doi: 10.1038/srep42651.
3
Importance of the alpha-amino group in the selective purification of synthetic histidine peptides by immobilised metal ion affinity chromatography.
J Chromatogr A. 1995 Jan 27;690(2):155-9. doi: 10.1016/0021-9673(94)01100-s.
4
Biological activities of histidine-rich peptides; merging biotechnology and nanomedicine.组氨酸丰富肽的生物学活性；融合生物技术和纳米医学。
Microb Cell Fact. 2011 Dec 2;10:101. doi: 10.1186/1475-2859-10-101.
5
2-Fluorohistidine--effects on protein synthesis in cell-free systems and in mouse L cells.
Biochem Pharmacol. 1979 May 1;28(9):1565-7. doi: 10.1016/0006-2952(79)90475-1.
6
Incorporation of 2-fluorohistidine in murine protein in vivo.
Life Sci. 1992;51(15):1197-204. doi: 10.1016/0024-3205(92)90356-t.
7
Biosynthetic incorporation of fluorohistidine into proteins in E. coli: a new probe of macromolecular structure.氟组氨酸在大肠杆菌中生物合成掺入蛋白质：一种大分子结构的新探针。
Chembiochem. 2005 Dec;6(12):2170-3. doi: 10.1002/cbic.200500249.
8
Mechanisms of metal-catalyzed oxidation of histidine to 2-oxo-histidine in peptides and proteins.肽和蛋白质中金属催化组氨酸氧化为2-氧代组氨酸的机制。
J Pharm Biomed Anal. 2000 Jan;21(6):1093-7. doi: 10.1016/s0731-7085(99)00182-x.
9
Immobilized palladium(II) ion affinity chromatography for recovery of recombinant proteins with peptide tags containing histidine and cysteine.固定化钯（II）离子亲和色谱法用于回收带有含组氨酸和半胱氨酸肽标签的重组蛋白。
J Mol Recognit. 2014 Nov;27(11):659-68. doi: 10.1002/jmr.2389.
10
The unusual metal ion binding ability of histidyl tags and their mutated derivatives.组氨酸标签及其突变衍生物独特的金属离子结合能力。
Dalton Trans. 2016 Apr 7;45(13):5629-39. doi: 10.1039/c5dt04747a. Epub 2016 Feb 29.
引用本文的文献
1
Non-canonical Amino Acid Substrates of E. coli Aminoacyl-tRNA Synthetases.原核生物氨酰-tRNA 合成酶的非典型氨基酸底物。
Chembiochem. 2022 Jan 5;23(1):e202100299. doi: 10.1002/cbic.202100299. Epub 2021 Sep 22.
2
In vitro genetic code reprogramming and expansion to study protein function and discover macrocyclic peptide ligands.体外遗传密码重编程和扩展，以研究蛋白质功能和发现大环肽配体。
Curr Opin Chem Biol. 2018 Oct;46:172-179. doi: 10.1016/j.cbpa.2018.07.013. Epub 2018 Aug 2.
3
Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase.通过编辑缺陷型氨酰-tRNA 合成酶将骨架修饰氨基酸掺入核糖体。
Org Biomol Chem. 2018 Feb 14;16(7):1073-1078. doi: 10.1039/c7ob02931d.
本文引用的文献
1
In Vitro Selection Combined with Ribosomal Translation Containing Non-proteinogenic Amino Acids.
Chem Rec. 2016 Feb;16(1):365-77. doi: 10.1002/tcr.201500239. Epub 2016 Jan 18.
2
Demystifying fluorine chemical shifts: electronic structure calculations address origins of seemingly anomalous (19)F-NMR spectra of fluorohistidine isomers and analogues.解读氟化学位移：电子结构计算揭示了氟组氨酸异构体及类似物看似异常的(19)F-NMR光谱的起源。
Phys Chem Chem Phys. 2015 Nov 11;17(45):30606-12. doi: 10.1039/c5cp05502d.
3
Kinetics of Ribosome-Catalyzed Polymerization Using Artificial Aminoacyl-tRNA Substrates Clarifies Inefficiencies and Improvements.使用人工氨酰-tRNA底物的核糖体催化聚合反应动力学阐明了低效性及改进方法。
ACS Chem Biol. 2015 Oct 16;10(10):2187-92. doi: 10.1021/acschembio.5b00335. Epub 2015 Jul 28.
4
mRNA display: from basic principles to macrocycle drug discovery.信使核糖核酸展示技术：从基本原理到大环药物发现
Drug Discov Today. 2014 Apr;19(4):388-99. doi: 10.1016/j.drudis.2013.10.011. Epub 2013 Oct 22.
5
Replacing amino acids in translation: expanding chemical diversity with non-natural variants.翻译：在翻译中替换氨基酸：用非天然变体扩展化学多样性。
Methods. 2013 Mar 15;60(1):70-4. doi: 10.1016/j.ymeth.2012.03.015. Epub 2012 Mar 28.
6
Reevaluation of the D-amino acid compatibility with the elongation event in translation.重新评估 D-氨基酸与翻译伸长事件的兼容性。
J Am Chem Soc. 2013 Feb 6;135(5):1830-7. doi: 10.1021/ja309570x. Epub 2013 Jan 25.
7
Monitoring anthrax toxin receptor dissociation from the protective antigen by NMR.通过核磁共振监测炭疽毒素受体与保护性抗原的解离
Protein Sci. 2009 Jan;18(1):17-23. doi: 10.1002/pro.26.
8
Ribosomal synthesis of N-methyl peptides.N-甲基肽的核糖体合成。
J Am Chem Soc. 2008 May 14;130(19):6131-6. doi: 10.1021/ja710016v. Epub 2008 Apr 11.
9
Synthesis of polyester by means of genetic code reprogramming.通过遗传密码重编程合成聚酯。
Chem Biol. 2007 Dec;14(12):1315-22. doi: 10.1016/j.chembiol.2007.10.015.
10
An expanded set of amino acid analogs for the ribosomal translation of unnatural peptides.用于非天然肽核糖体翻译的一组扩展氨基酸类似物。
PLoS One. 2007 Oct 3;2(10):e972. doi: 10.1371/journal.pone.0000972.
Zotero 插件