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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
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.
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C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

5.3K
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
5.3K
Allosteric Proteins-ATCase01:19

Allosteric Proteins-ATCase

5.8K
Binding sites linkages can regulate a protein's function.  For example, enzyme activity is often regulated through a feedback mechanism where the end product of the biochemical process serves as an inhibitor.
Aspartate transcarbamoylase (ATCase) is a cytosolic enzyme that catalyzes the condensation of L-aspartate and carbamoyl phosphate to  N-carbamoyl-L-aspartate. This reaction is the first step in pyrimidine biosynthesis. UTP and CTP, the end products of the pyrimidine synthesis...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
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
1.9K
Phase I Reactions: Hydrolytic Reactions01:15

Phase I Reactions: Hydrolytic Reactions

179
Hydrolysis, a cornerstone of phase I biotransformation reactions, uses water to cleave chemical bonds. This process is pivotal in drug metabolism, generating more polar metabolites that can be easily excreted.
An important hydrolytic reaction is ester hydrolysis. Ester bonds, often found in prodrugs, are broken down, increasing the solubility of drugs like aspirin and lidocaine for more straightforward elimination. Amide hydrolysis is another critical reaction, targeting amide bonds prevalent...
179

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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多重C−C結合分裂反応は,トリポルフィンテトラピロール生物合成酵素によって触媒化される

Richiro Ushimaru1,2,3, Jiaqi Lyu1, Meiqi Ling1

  • 1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.

Journal of the American Chemical Society
|April 19, 2023
PubMed
まとめ

トリポルフィンAの生物合成には,ヘム経路から分岐するユニークなC-C結合分裂反応が含まれています. 酵素HemF1,HemF2,およびTolIはコプロポリノゲンIIIを改変してトリポルフィンアグリコンコアを形成する.

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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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科学分野:

  • 生物化学
  • 自然製品の生物合成
  • 代謝経路

背景:

  • トリポルフィンAはテトラピロールの天然産物です
  • ペンダントデオキシ糖と非置換のピロールβサイトを特徴としています.
  • そのアグリコンコア生物合成は以前は記述されていなかった.

研究 の 目的:

  • トリポルフィンアグリコン核の生物合成経路を解明する.
  • その形成に関与する酵素と反応を特定する.
  • この経路が正規のヘム生物合成からどのように離れているかを理解する.

主な方法:

  • ヘム生物合成の中間物質を用いた酵素分析
  • 反応産物の特徴
  • HemF1,HemF2,およびTolIの酵素活性に関する分析

主要な成果:

  • HemF1は,コプロポルフィーリノゲンIIIの酸化分解を触媒化する.
  • HemF2は,残りのプロピオネート群をテトラビニル中間物質に処理する.
  • TolIはC-C結合の割れでビニル群を切り離し,非置換のピロールβサイトを生成する.

結論:

  • トリポルフィンアグリコンコアの生物合成には,新しいC-C結合分裂反応が含まれています.
  • これらの反応は,よく確立されたヘム生物合成経路から分岐する.
  • この研究は,天然の産物形成のためのユニークな代謝経路を明らかにしています.