• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

C-H 基团作为氢键供体:历史概述及在蛋白质和核酸中的存在。

C-H Groups as Donors in Hydrogen Bonds: A Historical Overview and Occurrence in Proteins and Nucleic Acids.

机构信息

Department of Molecular Physiology and Biological Physics, School of Medicine, University of Virginia, Charlottesville, VA 22903-2628, USA.

出版信息

Int J Mol Sci. 2023 Aug 24;24(17):13165. doi: 10.3390/ijms241713165.

DOI:10.3390/ijms241713165
PMID:37685972
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10488043/
Abstract

Hydrogen bonds constitute a unique type of non-covalent interaction, with a critical role in biology. Until fairly recently, the canonical view held that these bonds occur between electronegative atoms, typically O and N, and that they are mostly electrostatic in nature. However, it is now understood that polarized C-H groups may also act as hydrogen bond donors in many systems, including biological macromolecules. First recognized from physical chemistry studies, C-H…X bonds were visualized with X-ray crystallography sixty years ago, although their true significance has only been recognized in the last few decades. This review traces the origins of the field and describes the occurrence and significance of the most important C-H…O bonds in proteins and nucleic acids.

摘要

氢键是一种独特的非共价相互作用类型,在生物学中具有重要作用。直到最近,人们普遍认为这些键发生在电负性原子(通常是 O 和 N)之间,本质上主要是静电的。然而,现在人们已经认识到,在许多系统中,包括生物大分子,极性 C-H 基团也可以作为氢键供体。C-H…X 键最初是从物理化学研究中识别出来的,六十年前就通过 X 射线晶体学观察到了它们的存在,尽管直到最近几十年,人们才真正认识到它们的重要性。本综述追溯了该领域的起源,并描述了在蛋白质和核酸中最重要的 C-H…O 键的存在和意义。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/aea66ad5591e/ijms-24-13165-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/8061e1583215/ijms-24-13165-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/d569123d85b4/ijms-24-13165-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/f617b3848d30/ijms-24-13165-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/b1ba28d10738/ijms-24-13165-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/1246d73f8d8e/ijms-24-13165-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/b7a993652e44/ijms-24-13165-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/d6072994d7db/ijms-24-13165-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/3671daf6fac0/ijms-24-13165-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/d6a2dc8a5aff/ijms-24-13165-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/c7907b052694/ijms-24-13165-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/aea66ad5591e/ijms-24-13165-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/8061e1583215/ijms-24-13165-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/d569123d85b4/ijms-24-13165-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/f617b3848d30/ijms-24-13165-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/b1ba28d10738/ijms-24-13165-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/1246d73f8d8e/ijms-24-13165-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/b7a993652e44/ijms-24-13165-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/d6072994d7db/ijms-24-13165-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/3671daf6fac0/ijms-24-13165-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/d6a2dc8a5aff/ijms-24-13165-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/c7907b052694/ijms-24-13165-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/facd/10488043/aea66ad5591e/ijms-24-13165-g011.jpg

相似文献

1
C-H Groups as Donors in Hydrogen Bonds: A Historical Overview and Occurrence in Proteins and Nucleic Acids.C-H 基团作为氢键供体:历史概述及在蛋白质和核酸中的存在。
Int J Mol Sci. 2023 Aug 24;24(17):13165. doi: 10.3390/ijms241713165.
2
A structural role for tryptophan in proteins, and the ubiquitous Trp C-H...O=C (backbone) hydrogen bond.色氨酸在蛋白质中的结构作用,以及普遍存在的 Trp C-H…O=C(骨架)氢键。
Acta Crystallogr D Struct Biol. 2024 Jul 1;80(Pt 7):551-562. doi: 10.1107/S2059798324005515. Epub 2024 Jun 28.
3
Modulation of fragmental charge transfer via hydrogen bonds. Direct measurement of electronic contributions.通过氢键调节碎片电荷转移。电子贡献的直接测量。
J Phys Chem A. 2006 Jan 19;110(2):412-21. doi: 10.1021/jp052809+.
4
Evaluation of C-H cdots, three dots, centered O hydrogen bonds in native and misfolded proteins.天然和错误折叠蛋白质中C-H…O氢键的评估。
J Mol Biol. 2002 Sep 20;322(3):497-503. doi: 10.1016/s0022-2836(02)00785-4.
5
The orientation of N-H...O=C and N-H...N hydrogen bonds in biological systems: how good is a point charge as a model for a hydrogen bonding atom?生物系统中N-H...O=C和N-H...N氢键的取向:点电荷作为氢键原子模型的效果如何?
J Comput Aided Mol Des. 1997 Sep;11(5):479-90. doi: 10.1023/a:1007923124523.
6
C-H...O hydrogen bonds in the nuclear receptor RARgamma--a potential tool for drug selectivity.核受体RARγ中的C-H...O氢键——药物选择性的潜在工具
Structure. 2002 Sep;10(9):1197-204. doi: 10.1016/s0969-2126(02)00828-6.
7
A role for CH...O interactions in protein-DNA recognition.CH...O相互作用在蛋白质-DNA识别中的作用。
J Mol Biol. 1998 Apr 17;277(5):1129-40. doi: 10.1006/jmbi.1998.1660.
8
Short hydrogen bonds in proteins.蛋白质中的短氢键。
FEBS J. 2005 Apr;272(8):1819-32. doi: 10.1111/j.1742-4658.2005.04604.x.
9
Binding of genistein to the estrogen receptor based on an experimental electron density study.基于实验电子密度研究的染料木黄酮与雌激素受体的结合
J Am Chem Soc. 2007 Dec 5;129(48):15013-21. doi: 10.1021/ja075211j. Epub 2007 Nov 10.
10
NMR experiments for the rapid identification of P=O···H-X type hydrogen bonds in nucleic acids.用于快速鉴定核酸中P=O···H-X型氢键的核磁共振实验。
J Biomol NMR. 2017 Oct;69(2):101-110. doi: 10.1007/s10858-017-0140-7. Epub 2017 Oct 14.

引用本文的文献

1
Developing a Machine Learning Model for Hydrogen Bond Acceptance Based on Natural Bond Orbital Descriptors.基于自然键轨道描述符开发用于氢键接受的机器学习模型。
J Org Chem. 2025 Jul 18;90(28):9776-9788. doi: 10.1021/acs.joc.5c00724. Epub 2025 Jul 6.
2
Overview of Molecular Modeling in Drug Discovery with a Special Emphasis on the Applications of Artificial Intelligence.药物发现中的分子建模概述,特别强调人工智能的应用。
Methods Mol Biol. 2025;2952:1-13. doi: 10.1007/978-1-0716-4690-8_1.
3
Alpha and Omega Classification of β-Lactamase/Transpeptidase-like Superfamily Proteins Based on the Comparison of Their Structural Catalytic Cores.

本文引用的文献

1
The Realm of Unconventional Noncovalent Interactions in Proteins: Their Significance in Structure and Function.蛋白质中非常规非共价相互作用的领域:它们在结构和功能中的意义。
ACS Omega. 2023 Jun 13;8(25):22268-22284. doi: 10.1021/acsomega.3c00205. eCollection 2023 Jun 27.
2
Vibrational Solvatochromism Study of the C-H···O Improper Hydrogen Bond.C-H···O 非正常氢键的振动溶剂变色研究。
J Phys Chem B. 2023 May 4;127(17):3798-3805. doi: 10.1021/acs.jpcb.2c08119. Epub 2023 Apr 25.
3
Non-canonical DNA structures: Diversity and disease association.
基于β-内酰胺酶/转肽酶样超家族蛋白质结构催化核心比较的α和ω分类
Molecules. 2025 Apr 30;30(9):2019. doi: 10.3390/molecules30092019.
4
UFC1 reveals the multifactorial and plastic nature of oxyanion holes in E2 conjugating enzymes.UFC1揭示了E2共轭酶中氧阴离子洞的多因素和可塑性本质。
Nat Commun. 2025 Apr 25;16(1):3912. doi: 10.1038/s41467-025-58826-y.
5
Structural Catalytic Core in Subtilisin-like Proteins and Its Comparison to Trypsin-like Serine Proteases and Alpha/Beta-Hydrolases.枯草杆菌蛋白酶样蛋白的结构催化核心及其与胰蛋白酶样丝氨酸蛋白酶和 α/β-水解酶的比较。
Int J Mol Sci. 2024 Nov 5;25(22):11858. doi: 10.3390/ijms252211858.
6
Diverse Self-Assembled Molecular Architectures Promoted by C-H···O and C-H···Cl Hydrogen Bonds in a Triad of α-Diketone, α-Ketoimine, and an Imidorhenium Complex: A Unified Analysis Based on XRD, NEDA, SAPT, QTAIM, and IBSI Studies.由α-二酮、α-酮亚胺和铱配合物三元体系中C-H···O和C-H···Cl氢键促进形成的多种自组装分子结构:基于XRD、NEDA、SAPT、QTAIM和IBSI研究的统一分析
ACS Omega. 2024 Nov 2;9(45):45518-45536. doi: 10.1021/acsomega.4c07702. eCollection 2024 Nov 12.
7
Optimizing beet seed germination via dielectric barrier discharge plasma parameters.通过介质阻挡放电等离子体参数优化甜菜种子萌发
Heliyon. 2024 Oct 31;10(21):e40020. doi: 10.1016/j.heliyon.2024.e40020. eCollection 2024 Nov 15.
8
UCBShift 2.0: Bridging the Gap from Backbone to Side Chain Protein Chemical Shift Prediction for Protein Structures.UCBShift 2.0:从骨干到侧链蛋白质化学位移预测蛋白质结构的桥梁。
J Am Chem Soc. 2024 Nov 20;146(46):31733-31745. doi: 10.1021/jacs.4c10474. Epub 2024 Nov 12.
9
Hydrogen Bond Strengthens Acceptor Group: The Curious Case of the C-H···O=C Bond.氢键增强受氢体基团:C-H···O=C 键的奇异案例。
Int J Mol Sci. 2024 Aug 7;25(16):8606. doi: 10.3390/ijms25168606.
10
Exploring Novel GSK-3β Inhibitors for Anti-Neuroinflammatory and Neuroprotective Effects: Synthesis, Crystallography, Computational Analysis, and Biological Evaluation.探索新型 GSK-3β 抑制剂的抗神经炎症和神经保护作用:合成、晶体学、计算分析和生物学评价。
ACS Chem Neurosci. 2024 Sep 4;15(17):3181-3201. doi: 10.1021/acschemneuro.4c00365. Epub 2024 Aug 19.
非规范DNA结构:多样性与疾病关联
Front Genet. 2022 Sep 5;13:959258. doi: 10.3389/fgene.2022.959258. eCollection 2022.
4
Proline C-H Bonds as Loci for Proline Assembly via C-H/O Interactions.脯氨酸碳氢键作为通过碳氢键/氧相互作用进行脯氨酸组装的位点。
Chembiochem. 2022 Dec 16;23(24):e202200409. doi: 10.1002/cbic.202200409. Epub 2022 Nov 24.
5
Newly identified C-H⋯O hydrogen bond in histidine.组氨酸中新发现的 C-H⋯O 氢键。
Phys Chem Chem Phys. 2022 Aug 17;24(32):19233-19251. doi: 10.1039/d2cp02048c.
6
Understanding the role of non-Watson-Crick base pairs in DNA-protein recognition: Structural and energetic aspects using crystallographic database analysis and quantum chemical calculation.理解非 Watson-Crick 碱基对在 DNA-蛋白质识别中的作用:基于晶体数据库分析和量子化学计算的结构和能量方面。
Biopolymers. 2022 Jul;113(7):e23492. doi: 10.1002/bip.23492. Epub 2022 May 26.
7
Charge transfer across C-H⋅⋅⋅O hydrogen bonds stabilizes oil droplets in water.电荷在 C-H···O 氢键间转移稳定了水中的油滴。
Science. 2021 Dec 10;374(6573):1366-1370. doi: 10.1126/science.abj3007. Epub 2021 Dec 9.
8
On the centennials of the discoveries of the hydrogen bond and the structure of the water molecule: the short life and work of Eustace Jean Cuy (1897-1925).在氢键和水分子结构发现一百周年之际:尤斯塔斯·简·奎伊(Eustace Jean Cuy)的短暂生平与工作(1897-1925 年)。
Acta Crystallogr A Found Adv. 2021 Sep 1;77(Pt 5):362-378. doi: 10.1107/S2053273321006987. Epub 2021 Aug 13.
9
Trends in kinase drug discovery: targets, indications and inhibitor design.激酶药物研发趋势:靶点、适应症和抑制剂设计。
Nat Rev Drug Discov. 2021 Nov;20(11):839-861. doi: 10.1038/s41573-021-00252-y. Epub 2021 Aug 5.
10
Probing the Hydrogen-Bonding Environment of Individual Bases in DNA Duplexes with Isotope-Edited Infrared Spectroscopy.利用同位素编辑红外光谱研究 DNA 双螺旋中单个碱基的氢键环境。
J Phys Chem B. 2021 Jul 22;125(28):7613-7627. doi: 10.1021/acs.jpcb.1c01351. Epub 2021 Jul 8.