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NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

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Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Amino acids03:42

Amino acids

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Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible for...
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Noncovalent Attractions in Biomolecules02:35

Noncovalent Attractions in Biomolecules

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Noncovalent attractions are associations within and between molecules that influence the shape and structural stability of complexes. These interactions differ from covalent bonding in that they do not involve sharing of electrons.
Four types of noncovalent interactions are hydrogen bonds, van der Waals forces, ionic bonds, and hydrophobic interactions.
Hydrogen bonding results from the electrostatic attraction of a hydrogen atom covalently bonded to a strong-electronegative atom like oxygen,...
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Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
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蛋白质中的碳水化合物-芳香相互作用

Kieran L Hudson1, Gail J Bartlett1, Roger C Diehl2

  • 1School of Chemistry, University of Bristol , Bristol BS8 1TS, United Kingdom.

Journal of the American Chemical Society
|November 13, 2015
PubMed
概括

像托这样的芳香残留物是蛋白质与碳水化合物相互作用的关键. 电子和静电互补驱动这些重要的生物结合事件.

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科学领域:

  • 生物化学
  • 结构生物学
  • 分子相互作用

背景情况:

  • 蛋白质与碳水化合物之间的相互作用在生物过程中至关重要,
  • 定义和操纵这些相互作用对于理解健康和疾病至关重要.

研究的目的:

  • 量化分析带有碳水化合物的蛋白质的X射线晶体结构,以确定碳水化合物识别中的共同特征.
  • 阐明氨基酸侧链,特别是芳香残留在蛋白质-碳水化合物复合中的作用.

主要方法:

  • 对蛋白质-碳水化合物复合物的X射线晶体结构进行定量分析.
  • 核磁共振 (NMR) 光谱用于研究溶液中的碳水化合物-芳香相互作用.
  • 线性自由能量关系分析以支持电子效应.

主要成果:

  • 芳香氨基酸侧链,特别是基,在碳水化合物结合口袋中得到丰富.
  • 由于电子互补性,特定的碳水化合物C-H键优先与芳香残留物相互作用.
  • 核磁共振数据证实了碳水化合物中醇和电子贫乏的C-H键之间的有利结合,突出显示了静电贡献.

结论:

  • 碳水化合物和芳香残留物之间的静电和电子互补是蛋白质-碳水化合物复合的关键驱动因素.
  • 这些弱非共价相互作用决定了糖类在蛋白质结合部位中的特异性和定位.