関連する実験動画
Updated: May 28, 2026

08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
トリメチラミンN酸化物のメチル群は,水害性のインターフェイスから遠ざかっています
Laura B Sagle1, Katherine Cimatu, Vladislav A Litosh
1Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77843, USA.
Journal of the American Chemical Society
|October 5, 2011
まとめ
トリメチラミンN酸化物 (TMAO) は,メチル基を水害性の表面から遠ざけ,タンパク質の安定化作用は,インターフェースから優先的に除外することを示唆しています. これはタンパク質の折りたたみと安定性に影響を及ぼします.
科学分野:
- 生物物理化学 生物物理化学
- インタフェースサイエンスの科学
- タンパク質の安定化
背景:
- トリメチラミンN酸化物 (TMAO) は,オスモリートおよびタンパク質安定剤として知られています.
- インターフェースの分子行動を理解することは,タンパク質の安定性にとって極めて重要です.
- オスモライトのインターフェイスの方向性は,バイオ分子との相互作用に影響します.
研究 の 目的:
- TMAOの分子指向を水性/水害性の界面で調査する.
- TMAOのインターフェイス行動における構造の役割を明らかにする.
- TMAOのインターフェイス特性とタンパク質安定効果を結びつけるため.
主な方法:
- 振動総周波数スペクトロスコーピー (Vibrational Sum Frequency Spectroscopy,VSFS) を使用した.
- オクタデシルトリクロロシラン (OTS) /水のインターフェイスを研究しました.
- 異なるTMAO濃度で空気/水界面を調査した.
主要な成果:
- TMAOのメチル基は,水性OTSインターフェースから離れて,水相に向いていることが観察されました.
- 空気/水界面では,TMAOは配列を示したが,枯渇し,表面張力を増加させたことが判明した.
- 高濃度 (5M) でさえも,水中のぶら下がったOH群は,空気/水界面で持続した.
結論:
- TMAOの水害性インターフェイスからの指向と枯渇は,メチル基と酸化基の水害性の性質によって引き起こされます.
- 観察された枯渇は,TMAOのタンパク質安定化メカニズムにエントロピーが寄与していることを示唆しています.
- 分子指向と界面排除は,TMAOのタンパク質構造を安定させる能力の重要な要因である.
関連する概念動画
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...
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...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Stability of Substituted Cyclohexanes
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Chirality at Nitrogen, Phosphorus, and Sulfur
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
