Recent developments in catalytic amide bond formation

Todorovic, Mihajlo; Perrin, David M.

doi:10.1002/pep2.24210

Cited by 73 publications

(45 citation statements)

References 149 publications

(191 reference statements)

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“…Many general amidation protocols have been reported in literature. For an overview of existing protocols, we refer the reader to three recent reviews [ 11 , 12 , 13 ]. Furthermore, Fattahi et al [ 14 ] provided a comprehensive overview of synthetic methods for aromatic amides.…”

Section: Introductionmentioning

confidence: 99%

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

2022

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Phenol amides are bioactive compounds naturally present in many plants. This class of compounds is known for antioxidant, anti-inflammatory, and anticancer activities. To better understand the reactivity and structure–bioactivity relationships of phenol amides, a large set of structurally diverse pure compounds are needed, however purification from plants is inefficient and laborious. Existing syntheses require multiple steps, including protection of functional groups and are generally overly complicated and only suitable for specific combinations of hydroxycinnamic acid and amine. Thus, to facilitate further studies on these promising compounds, we aimed to develop a facile general synthetic route to obtain phenol amides with a wide structural diversity. The result is a protocol for straightforward one-pot synthesis of phenol amides at room temperature within 25 h using equimolar amounts of N,N′-dicyclohexylcarbodiimide (DCC), amine, hydroxycinnamic acid, and sodium bicarbonate in aqueous acetone. Eight structurally diverse phenol amides were synthesized and fully chemically characterized. The facile synthetic route described in this work is suitable for a wide variety of biologically relevant phenol amides, consisting of different hydroxycinnamic acid subunits (coumaric acid, ferulic acid, and sinapic acid) and amine subunits (agmatine, anthranilic acid, putrescine, serotonin, tyramine, and tryptamine) with yields ranging between 14% and 24%.

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Section: Introductionmentioning

confidence: 99%

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

2022

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“…Although reliable and reproducible automatic synthesis of nucleic acids and peptides are available, the production cost issue remains, especially for DNA origami requiring over a hundred ssDNAs with different length and sequence [ 123 ] Biotechnological mass production might be optional, whereas it poses additional issues such as sterilization and batch-to-batch variability, which could result in the increase in the production costs. It might be worth noting that catalytic peptide synthesis has attracted increasing attentions recently [ 124 , 125 , 126 , 127 , 128 ], which could overcome the production cost issue of peptides.…”

Section: Discussionmentioning

confidence: 99%

Supramolecular Architectures of Nucleic Acid/Peptide Hybrids

Higashi

Rozi

Hanifah

et al. 2020

IJMS

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Supramolecular architectures that are built artificially from biomolecules, such as nucleic acids or peptides, with structural hierarchical orders ranging from the molecular to nano-scales have attracted increased attention in molecular science research fields. The engineering of nanostructures with such biomolecule-based supramolecular architectures could offer an opportunity for the development of biocompatible supramolecular (nano)materials. In this review, we highlighted a variety of supramolecular architectures that were assembled from both nucleic acids and peptides through the non-covalent interactions between them or the covalently conjugated molecular hybrids between them.

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“…The -amino amide motif occurs frequently in biologically active molecules, and construction of this moiety poses an important problem for organic chemistry. [1][2][3][4] Polypeptide and amino acid amide synthesis via amide bond formation is highly refined, [5][6][7][8][9][10] however in contrast, methods for formation of the central -carbon-nitrogen bond are significantly less developed and remain a synthetic challenge. Methods for -amination of carbonyl groups are characterised by umpolung of either the amino or carbonyl fragments.…”

Section: Introductionmentioning

confidence: 99%

Direct alpha-Amination of Amides and Lactams Enabled by the (3+2) Vinyl Azide-Enolate Cycloaddition Manifold

Bell-Tyrer

Hume

Grant

et al. 2022

Preprint

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Direct alpha-amination of carbonyl compounds remains an important yet synthetically challenging transformation. Here we report a solution for direct alpha-amination of amides and lactams, identified through fundamental exploration of (3+2) vinyl azide-enolate cycloaddition chemistry. Initial cycloadducts undergo rearrangement via 1,2-N-migration to afford imine intermediates that are readily converted to the target alpha-amino amides or lactams. The sequence requires no pre-functionalisation, can be performed on a range of substrates, including compound classes unsuccessful using reported methods, and delivers primary or secondary alpha-amines. This work highlights the diversity and synthetic potential of the rapidly expanding (3+2) azide-enolate cycloaddition manifold.

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Recent developments in catalytic amide bond formation

Cited by 73 publications

References 149 publications

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

Supramolecular Architectures of Nucleic Acid/Peptide Hybrids

Direct alpha-Amination of Amides and Lactams Enabled by the (3+2) Vinyl Azide-Enolate Cycloaddition Manifold

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