Journal Article10.1021/ACS.CHEMREV.6B00237
Nonclassical Routes for Amide Bond Formation
764
TL;DR: The present review offers an overview of nonclassical (e.g., with no pre- or in situ activation of a carboxylic acid partner) approaches for the construction of amide bonds.
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Abstract: The present review offers an overview of nonclassical (e.g., with no pre- or in situ activation of a carboxylic acid partner) approaches for the construction of amide bonds. The review aims to comprehensively discuss relevant work, which was mainly done in the field in the last 20 years. Organization of the data follows a subdivision according to substrate classes: catalytic direct formation of amides from carboxylic and amines (section 2); the use of carboxylic acid surrogates (section 3); and the use of amine surrogates (section 4). The ligation strategies (NCL, Staudinger, KAHA, KATs, etc.) that could involve both carboxylic acid and amine surrogates are treated separately in section 5.
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Citations
Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative.
TL;DR: In this paper, an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant was reported.
43
Game Change from Reagent- to Substrate-Controlled Peptide Synthesis
TL;DR: An account of the development of Lewis-acid-catalyzed methods for racemization-free peptide synthesis is presented and these methods are based on the substrate control concept that has been exploited in this work.
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An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
TL;DR: In this paper, a Mo(CO)(6) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles was presented.
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Diboronic Acid Anhydride-Catalyzed Direct Peptide Bond Formation Enabled by Hydroxy-Directed Dehydrative Condensation.
TL;DR: The catalytic direct peptide bond formations via dehydrative condensation of β-hydroxy-α-amino acids, affording the serine, threonine, or β-Hydroxyvaline-derived peptides in high to excellent yields with high functional group tolerance, minimum epimerization, and excellent chemoselectivity are reported.
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Palladium-Catalyzed Amide Synthesis via Aminocarbonylation of Arylboronic Acids with Nitroarenes.
TL;DR: A palladium-catalyzed aminocarbonylation of aryl boronic acids with nitroarenes with a wide range of substrates provided a redox-economical process for the synthesis of amides and gave the corresponding amides in moderate to good yields.
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References
Synthesis of proteins by native chemical ligation
TL;DR: The technique of native chemical ligation is employable for chemically synthesizing full length proteins as discussed by the authors, which are chemically identical to proteins produced by cell free synthesis, and can be refolded and/or oxidized to form native disulfide-containing protein molecules.
3.3K
Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality
TL;DR: The bioorthogonal chemical reactions developed to date are described and how they can be used to study biomolecules.
A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases.
TL;DR: The effective range of physicochemical properties presented here can be used in the design of drug-like combinatorial libraries as well as in developing a more efficient corporate medicinal chemistry library.
2.5K
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TL;DR: A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is presented and should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions.
2.4K