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Molecular Models02:00

Molecular Models

Physical models representing molecular architectures of chemical compounds play essential roles in understanding chemistry. The use of molecular models makes it easier to visualize the structures and shapes of atoms and molecules.
Weak Acid Solutions04:02

Weak Acid Solutions

Few compounds act as strong acids. A far greater number of compounds behave as weak acids and only partially react with water, leaving a large majority of dissolved molecules in their original form and generating a relatively small amount of hydronium ions. Weak acids are commonly encountered in nature, being the substances partly responsible for the tangy taste of citrus fruits, the stinging sensation of insect bites, and the unpleasant smells associated with body odor. A familiar example of a...
Polyprotic Acids03:38

Polyprotic Acids

Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
Acid Strength and Molecular Structure03:05

Acid Strength and Molecular Structure

Binary Acids and Bases
In the absence of any leveling effect, the acid strength of binary compounds of hydrogen with nonmetals (A) increases as the H-A bond strength decreases down a group in the periodic table. For group 17, the order of increasing acidity is HF < HCl < HBr < HI. Likewise, for group 16, the order of increasing acid strength is H2O < H2S < H2Se < H2Te. Across a row in the periodic table, the acid strength of binary hydrogen compounds increases with increasing...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

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Determination of the Gas-phase Acidities of Oligopeptides
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Published on: June 24, 2013

ペプチドCH...Oの水素結合の溶液と固体モデル

Paul W Baures1, Alicia M Beatty, Muthu Dhanasekaran

  • 1Department of Chemistry, 111 Willard Hall, Kansas State University, Manhattan, Kansas 66506, USA. baures@signaturebio.com

Journal of the American Chemical Society
|September 19, 2002
PubMed
まとめ

この研究は,溶液と固体の両方のフマラミド誘導体におけるNH...O水素結合と同時にCH...O相互作用が起こることを示しています. これらの発見は,ペプチドとタンパク質の構造における類似の相互作用を理解するための貴重なモデルを提供します.

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科学分野:

  • 化学物理 化学物理
  • 分子生物学は分子生物学である.
  • クリスタルグラフィーです.

背景:

  • 非共性相互作用,特に水素結合は,分子構造と機能にとって極めて重要です.
  • CH...Oの相互作用は,従来のN-H...O結合よりも弱いが,ペプチドとタンパク質の構成を安定させる上で重要な役割を果たしている.
  • フマラミド誘導体は,これらの相互作用を調査するためのモデル化合物として機能します.

研究 の 目的:

  • フマラミド誘導体におけるCH...O相互作用の形成を特徴づけるために.
  • これらの相互作用を溶液と固体状態で比較する.
  • ペプチドおよびタンパク質構造におけるCH...O相互作用のモデルとしてフマラミド誘導体を確立する.

主な方法:

  • 1H核磁気共振 (NMR) スペクトロスコーピーを用いて溶液分析.
  • X線結晶学を用いた固体分析.
  • クロロフォーム-d (CDCl3) でデュテラートジメチル硫酸化物 (DMSO-d6) を用いたタイトリング実験.

主要な成果:

  • 1H NMRスペクトロスコーピーは,NH...O=S(CD3) 2の水素結合と並行して,CH...O=S(CD3) 2の水素結合に関与するCH群のダウンフィールド化学的シフトを明らかにしました.
  • 非参加CH群は,より高いDMSO-d6濃度で最小の化学シフト変化または上位シフトを示しました.
  • X線結晶構造は,分子間NH...O=C水素結合とともにCH...O=C水素結合の存在を確認した.

結論:

  • 溶液NMRと固体結晶学の両方が,フマラミド誘導体における同時に発生するCH...OとNH...Oの水素結合の証拠を提供している.
  • 結晶構造における観測されたCH...O=Cの水素結合は,タンパク質の反パラレルベータシート構造に見られるものと似ている.
  • フマラミド誘導体は,ペプチドとタンパク質の構造的安定性に関連するCH...O相互作用を効果的にモデル化します.