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Related Concept Videos

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.0K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.0K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.9K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
3.2K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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A facile method for vancomycin C-terminus functionalization and derivatization through hydrazide.

Yu Hu1, Xiangman Zou2, Weiwei Shi3

  • 1School of Pharmacy, Jinzhou Medical University, Jinzhou 121001, PR China; CAS Key Laboratory of Receptor Research, CAS Center for Excellence in Molecular Cell Science, Center for Biotherapeutics Discovery Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, PR China.

Bioorganic & Medicinal Chemistry Letters
|April 11, 2021
PubMed
Summary

A novel method enables vancomycin C-terminus modification, creating new derivatives to combat vancomycin-resistant bacteria. This strategy enhances antibacterial activity against resistant strains.

Keywords:
Antibacterial activityHydrazide derivativesNative Chemical LigationVancomycin C-terminus modification

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Microbiology

Background:

  • Clinical use of vancomycin has led to vancomycin-resistant bacteria.
  • Vancomycin analogues like Telavancin, Oritavancin, and Dalbavancin have been developed.
  • Modifying the vancomycin C-terminus can enhance activity against resistant strains.

Purpose of the Study:

  • To develop a facile strategy for vancomycin C-terminus functionalization and derivatization.
  • To create novel vancomycin derivatives with improved antibacterial properties.
  • To explore the conjugation of peptides and lipophilic structures to the vancomycin C-terminus.

Main Methods:

  • A native chemical ligation-inspired strategy was employed for vancomycin C-terminus functionalization.
  • Vancomycin was derivatized with a C-terminal hydrazide moiety.
  • Cysteine-containing peptides and lipophilic structures were conjugated via the hydrazide group.
  • Fluorescent FITC-vancomycin was synthesized using Cys-Maleimide conjugation.

Main Results:

  • A facile method for vancomycin C-terminus functionalization using hydrazide was established.
  • Conjugation of cysteine-containing peptides and lipophilic moieties to vancomycin was achieved.
  • Fluorescently labeled vancomycin derivatives were successfully prepared.
  • The synthesized vancomycin derivatives were tested against Gram-positive and Gram-negative bacteria.

Conclusions:

  • The developed hydrazide-based strategy provides an accessible route for vancomycin C-terminus modification.
  • Functionalized vancomycin derivatives show potential for combating vancomycin-resistant bacteria.
  • This approach allows for the introduction of diverse structures to enhance antibacterial efficacy.