异体性合与双边β-转结构的阿扎酸,带有两个遥远的性中心
Xiaosheng Yan1,2, Jinlian Cao1, Huan Luo1
1MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
Nature communications
|October 29, 2024
概括
这项研究展示了一种新的酶选择性合成方法,用于制造异体的双边阿扎. 反应会优先形成异体基质产物而不是同体基质产物,即使有遥远的基质中心.
科学领域:
- 有机化学 有机化学
- 不对称的合成方法
- 超分子化学 超分子化学
背景情况:
- 选择性合成通常依赖于性催化剂或辅助剂.
- 在没有奇拉诱导的情况下,与遥远的立体中心实现enantioselectivity是具有挑战性的.
研究的目的:
- 开发一种方法,用于双边阿扎的enantioselective合成,没有性催化剂或辅助剂.
- 为了研究一反应中异体基质产品与同体基质产品的形成.
主要方法:
- 拉塞姆化物与阿基拉尔1,4-bis(异酸) 的单反应.
- 对产品立体化学和晶体结构的分析.
主要成果:
- 偏好形成异构体双边阿扎,而不是同构体的.
- 异构体产物通过分子间键形成超分子螺旋超结构.
- 类人体产品采用不太稳定的β片结构.
结论:
- 通过生物模拟超结构的形成,可以实现具有遥远性中心的分子的酶选择合成.
- 分子间相互作用和超分子组合在指导反选择性方面发挥着关键作用.
- 这种方法提供了控制复杂分子合成中的酶选择性新策略.
相关概念视频
Prochirality
3.8K
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...
3.8K
Molecules with Multiple Chiral Centers
11.3K
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...
11.3K
Chirality in Nature
13.0K
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.
13.0K
Chirality at Nitrogen, Phosphorus, and Sulfur
5.7K
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...
5.7K
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
1.5K
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...
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
1.5K
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...
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


