ポイント・ツー・アクシアル・キラリティ・トランスファー - モノアミンの絶対的構成を"感知"するための新しい探査機

Mercy Anyika¹, Hadi Gholami, Kumar D Ashtekar

¹Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.

Journal of the American Chemical Society

|December 6, 2013

まとめ

新しい宿主分子は,アミンの分子認識とキラリティ感知を可能にします. この宿主は,水素結合とエクシトン結合の円形二重化を用いてアミンのキラリティを予測し,化学分析のための新しいツールを提供している.

科学分野:

超分子化学超分子化学
チラルセンシング (Chiral Sensing) とは
スペクトル顕微鏡検査です.

背景:

分子認識とヒラリティ感知は,化学と生物学において極めて重要です.
ゲスト分子のキラリティを決定するための選択的で敏感な方法の開発は,依然として課題です.

研究の目的:

分子認識とキラリティセンシングのための新しい宿主分子を記述する.
宿主のキラルアミンを結合し,検出可能な信号を誘導する能力を調査する.
結合ゲスト分子のキラリティを予測するためのモデルを提案する.

主な方法:

PまたはMヘリシティを採用できるビフェノール核を持つ宿主分子の合成.
水素結合相互作用を利用したキラルアミンとの結合研究.
ディアステレオメア複合体の形成とヘリシティの好みの分析.
エクシトン結合円二極化 (ECCD) スペクトロスコーピーを用いてキラリティの検出.

主要な成果:

宿主分子は,水素結合を通じてキラルアミンを結束することに成功します.
ディアステレオメア複合体の形成は,PまたはMヘリシティのどちらかを好むことにつながります.
結合腔内のステリック相互作用が誘導ヘリシティを決定する.
検出可能なECCDスペクトルが生成され,結合アミンのキラリティと相関する.
結合アミンキラリティの非経験的予測のための作業モデルが確立される.

結論:

説明されている宿主分子は,アミンの分子認識とキラリティ感知に有効です.
誘導ヘリシティとECCD信号は,アミンキラリティを決定するための信頼できる方法を提供します.
提案されたモデルは,キラルなゲスト-ホストの相互作用を理解するための予測ツールを提供します.

さらに関連する動画

08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

9.6K

14:55

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Published on: September 17, 2017

16.8K

関連する概念動画

02:05

Prochirality

4.0K

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

4.0K

00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

3.7K

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...

3.7K

02:30

Chirality in Nature

13.5K

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

13.5K

02:25

Chirality

23.4K

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

23.4K

02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

5.5K

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...

5.5K

02:25

Molecules with Multiple Chiral Centers

11.6K

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...