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関連する概念動画

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

2.9K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
2.9K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.1K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.1K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.0K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.0K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.3K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.3K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.4K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.4K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.7K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.7K

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関連する実験動画

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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中環のラクトンを形成するポリケチド・サイクラス

De-Wei Gao, Cooper S Jamieson, Gaoqian Wang1

  • 1State Key Laboratory of Bio-organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, China.

Journal of the American Chemical Society
|December 22, 2020
PubMed
まとめ

研究者らは,中環乳糖化を効率的に触媒化するチオエステラゼ酵素DcsBを発見した. この酵素は,デカレストリクチンC1経路から,広範囲の基板範囲を示し,ラクトン合成に挑戦するバイオ触媒としての可能性を秘めています.

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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関連する実験動画

Last Updated: Nov 24, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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科学分野:

  • 生物化学
  • 有機化学
  • 酵素学

背景:

  • 中環ラクトンは,不利なサイクルエネルギーにより合成が困難である.
  • デカレストリクチンのC1生物合成経路は,複雑な天然産物形成を伴う.

研究 の 目的:

  • 中環ラクトンの形成に関与する酵素を特定し,特徴づけること.
  • ラクトニゼーション反応の生物触媒としてのDcsBの可能性を調査する.

主な方法:

  • デカレストリクチンのC1経路からの酵素発見と分離.
  • DcsBの活性と基質の範囲を評価するための生化学的測定
  • 触媒メカニズムの解明のためのX線結晶学と計算モデリング.

主要な成果:

  • 中環ラクトニゼーションを効率的に触媒する酵素であるチオエステラーゼDcsBの発見.
  • DcsBは,異なる長さの線形前駆体と置換体との広範な基板乱交性を表しています.
  • 構造と計算分析により,DcsBの触媒作用の分子基盤が明らかになった.

結論:

  • DcsBは,合成の課題を克服する中環ラクトニゼーションの非常に効果的な酵素です.
  • 酵素の広範囲の基質は,様々なラクトン合成の応用のための有望な生物触媒となります.
  • DcsBのメカニズムの理解は,挑戦的なサイクライゼーションの酵素制御の洞察を提供します.