肽键等排体评价
An evaluation of peptide-bond isosteres.
机构信息
Graduate Program in Biophysics, University of Wisconsin-Madison, Madison, WI 53706-1534, USA.
出版信息
Chembiochem. 2011 Aug 16;12(12):1801-7. doi: 10.1002/cbic.201100272. Epub 2011 Jul 12.
Abstract
Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partake in noncovalent interactions is compared with that of the peptide bond. The consequential perturbations provide a useful tool for chemical biologists to reveal new structure-function relationships, and to endow peptides and proteins with desirable attributes.
摘要
肽键类似物可以通过放大或削弱特定的化学性质，对肽或蛋白质的结构和功能进行深入研究。在这篇综述中，详细研究了四种类似物——硫酰胺、酯、烯烃和氟烯烃的电子、结构和构象特性。特别是，比较了这些类似物参与非共价相互作用的能力与肽键的能力。由此产生的扰动为化学生物学家提供了一种有用的工具，可以揭示新的结构-功能关系，并赋予肽和蛋白质所需的属性。
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本文引用的文献
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ARKIVOC. 2010 Jul 8;2010:251-262.
2
Chemoselectivity in chemical biology: acyl transfer reactions with sulfur and selenium.化学生物学中的化学选择性：含硫和硒的酰基转移反应。
Acc Chem Res. 2011 Sep 20;44(9):752-61. doi: 10.1021/ar200081s. Epub 2011 Jun 3.
3
Signature of n→π* interactions in α-helices.α-螺旋中 n→π* 相互作用的特征。
Protein Sci. 2011 Jun;20(6):1077-81. doi: 10.1002/pro.627. Epub 2011 Apr 26.
4
n-->pi* interactions in proteins.蛋白质中的 n—>pi* 相互作用。
Nat Chem Biol. 2010 Aug;6(8):615-20. doi: 10.1038/nchembio.406. Epub 2010 Jul 11.
5
n --> pi* Interaction and n)(pi Pauli repulsion are antagonistic for protein stability.n-π*相互作用和 n)(π 保罗排斥对于蛋白质稳定性是拮抗的。
J Am Chem Soc. 2010 May 19;132(19):6651-3. doi: 10.1021/ja100931y.
6
Quantum mechanical origin of the conformational preferences of 4-thiaproline and its S-oxides.量子力学对 4-硫代脯氨酸及其 S-氧化物构象偏好的起源。
Amino Acids. 2011 Jun;41(1):181-6. doi: 10.1007/s00726-010-0504-8. Epub 2010 Mar 12.
7
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J Am Chem Soc. 2009 Sep 30;131(38):13728-32. doi: 10.1021/ja904177k.
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9
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10
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