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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination reactions can be...

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Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition
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Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition

Published on: December 23, 2016

Bioconjugation with strained alkenes and alkynes.

Marjoke F Debets1, Sander S van Berkel, Jan Dommerholt

  • 1Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ, The Netherlands.

Accounts of Chemical Research
|July 20, 2011
PubMed
Summary

Organic chemists utilize strain-promoted cycloadditions of strained alkenes and alkynes for precise bioconjugation. These bioorthogonal reactions enable selective modification of biomolecules within living systems, advancing chemical biology research.

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Area of Science:

  • Chemical Biology
  • Organic Synthesis
  • Bioconjugation Chemistry

Background:

  • Organic chemists have long been inspired by complex natural products, driving the development of synthetic strategies.
  • Modifying biological molecules like proteins and nucleic acids requires mild, precise chemical transformations known as bioconjugation.
  • Bioorthogonal reactions, which function within living cells, represent a significant challenge and opportunity in chemical biology.

Purpose of the Study:

  • To review advancements in bioconjugation strategies centered on cycloadditions involving strained unsaturated systems.
  • To highlight the development and application of strain-promoted cycloadditions in chemical biology.
  • To discuss the utility of strained alkenes and alkynes in creating novel bioorthogonal reactions.

Main Methods:

  • Exploration of cycloaddition reactions involving strained alkenes and alkynes with various reaction partners.
  • Investigation of strain-promoted cycloadditions, including oxanobornadienes with azides and reactions of cyclooctynes.
  • Application of these reactions for the modification of biopolymers such as nucleic acids, proteins, and glycans.

Main Results:

  • Strained unsaturated systems, particularly strained alkenes and alkynes, exhibit unique reactivity in cycloaddition reactions.
  • Strain-promoted cycloadditions have been refined into valuable tools for precise biopolymer modification.
  • Cyclooctynes, due to their strained triple bonds, demonstrate high reactivity, enabling reagent-free bioconjugations.

Conclusions:

  • Strain-promoted cycloadditions of strained alkenes and alkynes are powerful tools in modern chemical biology.
  • These bioorthogonal reactions offer unprecedented possibilities for studying biological systems.
  • The development of these reactions facilitates precise modification of biomolecules in complex biological environments.