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Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

3.5K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
3.5K
Structure of Amines01:19

Structure of Amines

2.6K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
2.6K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.5K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

2.8K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
2.8K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.4K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.4K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.1K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
6.1K

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関連する実験動画

Updated: Jul 11, 2025

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

9.7K

アミン反応性プローブとしてスクワレットを評価する

Katherine I Taylor1, Jordan S Ho1, Hallie O Trial1

  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|November 8, 2023
PubMed
まとめ
この要約は機械生成です。

スクワリックエステルとスクワラミドは軽い電ophilesとして作用し,タンパク質結合部位内のライシン残基の選択的共性ラベリングを可能にします. この選択性は 効果的な化学タンパク質探査機の開発に不可欠です

さらに関連する動画

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

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Determination of the Gas-phase Acidities of Oligopeptides
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Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

11.2K

関連する実験動画

Last Updated: Jul 11, 2025

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
09:46

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

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Determination of the Gas-phase Acidities of Oligopeptides
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Determination of the Gas-phase Acidities of Oligopeptides

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科学分野:

  • 化学生物学
  • 有機化学
  • 生物化学

背景:

  • タンパク質の結合部位を特定するために,共性探知器は不可欠です.
  • ライシン残基は多量に存在し,共性探査機にとって魅力的な標的である.
  • 結合部位ライシンでアミン特異的および地域選択的反応を達成することは大きな課題です.

研究 の 目的:

  • スクワレートとスクワラミドがリジン残留物に対する選択的共性ラベル剤としての可能性を調査する.
  • スクワレート/スクワラミドの反応性と選択性を他のアミン反応性電ophilesと比較する.
  • 血縁性に基づく化学タンパク質の応用におけるスクワレットの有用性を評価する.

主な方法:

  • アミンとスクワレートとモノスクワラミドの反応の運動分析.
  • スクアレート反応性をN-ヒドロキシスッキニミジルエステルなどの他の生物結合ハンドルと比較する.
  • Mycobacterium tuberculosisのGlfT2酵素を用いたスクワレート選択性の評価.この酵素は多重な表面露出ライシンを有する.

主要な成果:

  • モノスクワラミドは軽度の電離性を示し,選択的なライシンラベル付けの長期滞在時間を好みます.
  • スクワレート反応性は置換剤によって調節され,電子取り除くグループとディチオノスクワレートは反応性を高めます.
  • N-ヒドロキシスッキニミジルエステルは,より早く反応し,選択性が低いことを示しています.
  • スクワレートは,GlfT2のラベル付けにおいて高い選択性を示し,主に結合部位付近の単一のライシンを修正し,共性抑制につながった.

結論:

  • スクワリックエステルとスクワラミドは,ライシン残留物の有効で選択的な共性ラベリング剤です.
  • 調節可能な反応性と選択性により,親和性ベースの化学タンパク質学にとって貴重なツールになります.
  • これらの発見は,タンパク質とリガンドの相互作用を特定し,研究するための改善された方法の道を開く.