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Published on: December 23, 2016
Arylation Chemistry for Bioconjugation.
Chi Zhang1, Ekaterina V Vinogradova1,2, Alexander M Spokoyny1,3
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139, USA.
New bioconjugation methods create modified biomolecules with novel functions. These strategies focus on forming nucleophile-sp2 carbon bonds for versatile applications in peptide, protein, sugar, and nucleic acid modification.
Area of Science:
- Bioconjugation Chemistry
- Organic Chemistry
- Biochemistry
Background:
- Bioconjugation chemistry enables the creation of modified biomolecules with enhanced functionalities.
- Developing efficient and selective bioconjugation reactions under mild conditions is crucial for biomolecule modification.
Purpose of the Study:
- To review sulfur, nitrogen, selenium, oxygen, and carbon arylative bioconjugation strategies.
- To highlight the applications of these strategies in modifying peptides, proteins, sugars, and nucleic acids.
Main Methods:
- Focus on bioconjugation methods forming nucleophile-sp2 carbon bonds.
- Review of various arylative bioconjugation strategies.
- Application of these methods to diverse biomolecules.
Main Results:
- Demonstration of versatile bioconjugation techniques.
- Creation of modified biomolecules with novel and enhanced functions.
- Successful modification of peptides, proteins, sugars, and nucleic acids.
Conclusions:
- Nucleophile-sp2 carbon bond-forming reactions are promising for novel bioconjugate synthesis.
- Arylative bioconjugation offers a powerful toolkit for biomolecule engineering.
- These advancements expand the functional capabilities of biomolecules beyond their natural scope.
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Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids
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Preparation of Alkynes: Alkylation Reaction
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.

