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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

13.5K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
13.5K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

18.2K
Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
18.2K
SN1 Reaction: Kinetics02:05

SN1 Reaction: Kinetics

10.0K
In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...
10.0K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

13.0K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
13.0K
Oxidation of Alcohols02:37

Oxidation of Alcohols

18.2K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
18.2K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.7K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.7K

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関連する実験動画

Updated: Mar 30, 2026

Assessing Energy Substrate Oxidation In Vitro with 14CO2 Trapping
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Assessing Energy Substrate Oxidation In Vitro with 14CO2 Trapping

Published on: March 23, 2022

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TET媒介による酸化に対する基質の好みに関する構造的洞察

Lulu Hu1,2,3, Junyan Lu4, Jingdong Cheng1,2

  • 1Fudan University Shanghai Cancer Center, Institute of Biomedical Sciences, Shanghai Medical College of Fudan University, Shanghai 200032, China.

Nature
|November 3, 2015
PubMed
まとめ

10−11 転位 (TET) タンパク質はDNAメチル化を酸化する. TET1とTET2は,基質構成と酸化効率により,5-ヒドロキシメチルシトシン (5hmC) または5-ホルミルシトシン (5fC) よりも,5メチルシトシン (5mC) に高い活性を示しています. これは5hmCが 安定した表遺伝子マークであることを示唆しています

さらに関連する動画

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

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関連する実験動画

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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

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科学分野:

  • エピジェネティクス
  • 分子生物学
  • 生物化学

背景:

  • DNAメチル化が 重要な表遺伝子調節因子です
  • 10−11 転位 (TET) タンパク質は,5-メチルサイトシン (5mC) を酸化することによってDNA脱メチル化を媒介する.
  • TETタンパク質は,5mCを5hydroxymethylcytosine (5hmC),5-formylcytosine (5fC),および5-carboxylcytosine (5caC) に繰り返し変換する.

研究 の 目的:

  • 人間のTET1およびTET2タンパク質の基板偏好を調査する.
  • 異なるDNAメチル化誘導体に対するTETタンパク質の構造的基礎を解明する.
  • エピジェネティックマークとしての5hmCの安定性に対するTETタンパク質の影響を理解する.

主な方法:

  • TET2-5hmC-DNAおよびTET2-5fC-DNA複合体の結晶構造の決定
  • TETタンパク質の活性と基質の酸化効率の生化学的分析
  • 5mC,5hmC,および5fC基板によるTET2DNA複合体の比較構造分析

主要な成果:

  • 人間のTET1とTET2は,5mC-DNAに対する酵素活性が,5hmC-DNAと5fC-DNAと比較して高い.
  • 結晶構造は,TET2触媒腔内の5mC,5hmC,および5fCの類似の結合を明らかにしますが,改変された塩基の異なる方向性があります.
  • 生化学的なデータは,5hmCと5fCの制限された構成が効率的な水素抽出を阻害し,これらの基板の触媒効率を低下させることを示しています.

結論:

  • TETタンパク質の基板の好みは,5mC誘導体の固有特性,特に改変されたサイトシン基体の形状と水素結合能力によって決定される.
  • 5hmCに対するTETタンパク質の反応性の低下は,それが比較的安定した表遺伝子マークであることを示唆する.
  • TETタンパク質は進化的に最適化され,5hmCを生成し維持し,様々な規制機能を果たす可能性があります.