Peptide bond ≈ Peptide bond
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Breaking Amides using Nickel Catalysis Open
Amides have been widely studied for decades, but their synthetic utility has remained limited in reactions that proceed with rupture of the amide C-N bond. Using Ni catalysis, we have found that amides can now be strategically employed in …
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The <i>n</i>→π* Interaction Open
The carbonyl group holds a prominent position in chemistry and biology not only because it allows diverse transformations but also because it supports key intermolecular interactions, including hydrogen bonding. More recently, carbonyl gro…
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Approaching infinite affinity through engineering of peptide–protein interaction Open
Much of life’s complexity depends upon contacts between proteins with precise affinity and specificity. The successful application of engineered proteins often depends on high-stability binding to their target. In recent years, various app…
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Cell Wall Hydrolases in Bacteria: Insight on the Diversity of Cell Wall Amidases, Glycosidases and Peptidases Toward Peptidoglycan Open
The cell wall (CW) of bacteria is an intricate arrangement of macromolecules, at least constituted of peptidoglycan (PG) but also of (lipo)teichoic acids, various polysaccharides, polyglutamate and/or proteins. During bacterial growth and …
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Ester‐Mediated Amide Bond Formation Driven by Wet–Dry Cycles: A Possible Path to Polypeptides on the Prebiotic Earth Open
Although it is generally accepted that amino acids were present on the prebiotic Earth, the mechanism by which α‐amino acids were condensed into polypeptides before the emergence of enzymes remains unsolved. Here, we demonstrate a prebioti…
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Translation in Prokaryotes Open
This review summarizes our current understanding of translation in prokaryotes, focusing on the mechanistic and structural aspects of each phase of translation: initiation, elongation, termination, and ribosome recycling. The assembly of t…
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Amide Bond Formation Strategies: Latest Advances on a Dateless Transformation Open
The synthesis of amides remains one of the most important transformations and it is one of the more frequently performed reactions. In the pharmaceutical industry, the formation of the amide group is pivotal and among the more important tr…
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Cross-Coupling of Amides by N–C Bond Activation Open
In recent years, significant conceptual advances have taken place in the field of amide bond cross-coupling. Mild and selective functionalization of amides by transition-metal catalysis has an enormous potential for widespread applications…
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Amide Bond Activation of Biological Molecules Open
Amide bonds are the most prevalent structures found in organic molecules and various biomolecules such as peptides, proteins, DNA, and RNA. The unique feature of amide bonds is their ability to form resonating structures, thus, they are hi…
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Peptide ligation by chemoselective aminonitrile coupling in water Open
Amide bond formation is one of the most important reactions in both chemistry and biology1-4, but there is currently no chemical method of achieving α-peptide ligation in water that tolerates all of the 20 proteinogenic amino acids at the …
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Nickel‐Catalyzed Esterification of Aliphatic Amides Open
Recent studies have demonstrated that amides can be used in nickel‐catalyzed reactions that lead to cleavage of the amide C−N bond, with formation of a C−C or C−heteroatom bond. However, the general scope of these methodologies has been re…
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Context-specific inhibition of translation by ribosomal antibiotics targeting the peptidyl transferase center Open
Significance Chloramphenicol and linezolid interfere with translation by targeting the ribosomal catalytic center and are viewed as universal inhibitors of peptide bond formation. We show that, contrary to this view, the activity of these …
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Structural Insights into Thioether Bond Formation in the Biosynthesis of Sactipeptides Open
Sactipeptides are ribosomally synthesized peptides that contain a characteristic thioether bridge (sactionine bond) that is installed posttranslationally and is absolutely required for their antibiotic activity. Sactipeptide biosynthesis r…
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The E3 ligase HOIL-1 catalyses ester bond formation between ubiquitin and components of the Myddosome in mammalian cells Open
Significance The formation of isopeptide bonds between the C-terminal carboxylate of ubiquitin and ε-amino groups of lysine residues on another protein is a major mechanism for regulating protein function. Ubiquitin can also form peptide b…
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Palladium‐Mediated Arylation of Lysine in Unprotected Peptides Open
A mild method for the arylation of lysine in an unprotected peptide is presented. In the presence of a preformed biarylphosphine‐supported palladium(II)–aryl complex and a weak base, lysine amino groups underwent C−N bond formation at room…
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<i>N</i>‐Acyl‐Glutarimides: Privileged Scaffolds in Amide N–C Bond Cross‐Coupling Open
In this Microreview, we describe the recent exciting developments in the burgeoning area of amide N–C cross‐coupling enabled by amide bond twist of N ‐acyl‐glutarimides. Since the initial reports in 2015, these amides have been demonstrate…
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A combined cryo-EM and molecular dynamics approach reveals the mechanism of ErmBL-mediated translation arrest Open
Nascent polypeptides can induce ribosome stalling, regulating downstream genes. Stalling of ErmBL peptide translation in the presence of the macrolide antibiotic erythromycin leads to resistance in Streptococcus sanguis . To reveal this st…
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Aqueous microdroplets enable abiotic synthesis and chain extension of unique peptide isomers from free amino acids Open
Amide bond formation, the essential condensation reaction underlying peptide synthesis, is hindered in aqueous systems by the thermodynamic constraints associated with dehydration. This represents a key difficulty for the widely held view …
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Atom-economic catalytic amide synthesis from amines and carboxylic acids activated in situ with acetylenes Open
Amide bond-forming reactions are of tremendous significance in synthetic chemistry. Methodological research has, in the past, focused on efficiency and selectivity, and these have reached impressive levels. However, the unacceptable amount…
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“Newton’s cradle” proton relay with amide–imidic acid tautomerization in inverting cellulase visualized by neutron crystallography Open
A study of the visualization of proton relay in cellulase by neutron crystallography.
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Photolabile Linkers: Exploiting Labile Bond Chemistry to Control Mode and Rate of Hydrogel Degradation and Protein Release Open
Photolabile moieties have been utilized in applications ranging from peptide synthesis and controlled protein activation to tunable and dynamic materials. The photochromic properties of nitrobenzyl (NB) based linkers are readily tuned to r…
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Understanding How Prolyl-4-hydroxylase Structure Steers a Ferryl Oxidant toward Scission of a Strong C–H Bond Open
Prolyl-4-hydroxylase (P4H) is a non-heme iron hydroxylase that regio- and stereospecifically hydroxylates proline residues in a peptide chain into R-4-hydroxyproline, which is essential for collagen cross-linking purposes in the human body…
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Carbodiimide Induced Cross-Linking, Ligand Addition, and Degradation in Gelatin Open
The water-soluble carbodiimide, 1-ethyl-3-(3-(dimethylaminopropyl)-carbodiimide (EDC) is widely used in protein chemistry. We used EDC-induced gelatin cross-linking as a model for amide bond formation to resolve reaction ambiguities with c…
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A protocol for amide bond formation with electron deficient amines and sterically hindered substrates Open
A protocol for amide coupling by in situ formation of acyl fluorides and reaction with amines at elevated temperature has been developed and found to be efficient for coupling of sterically hindered substrates and electron deficient amines…
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Adenylation Activity of Carboxylic Acid Reductases Enables the Synthesis of Amides Open
Carboxylic acid reductases (CARs) catalyze the reduction of a broad range of carboxylic acids to aldehydes using the cofactors adenosine triphosphate and nicotinamide adenine dinucleotide phosphate, and have become attractive biocatalysts …
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Biocatalytic amide bond formation Open
The state-of-the-art of biocatalytic amide bond formation is discussed with the help of a manually curated database of enzymatic amidation reactions.
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The Dawn of Metal-Oxo Clusters as Artificial Proteases: From Discovery to the Present and Beyond Open
The selective cleavage of peptide bonds in proteins is of paramount importance in many areas of the biological and medical sciences, playing a key role in protein structure/function/folding analysis, protein engineering, and targeted prote…
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Structural and mutational analysis of the nonribosomal peptide synthetase heterocyclization domain provides insight into catalysis Open
Significance Nonribosomal peptide synthetases produce peptides with wide varieties of therapeutic and biological activities. Monomer substrates are typically linked by a condensation domain. However, in many modules, a heterocyclization (C…
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Transformation of a [4+6] Salicylbisimine Cage to Chemically Robust Amide Cages Open
In recent years, interest in shape‐persistent organic cage compounds has steadily increased, not least because dynamic covalent bond formation enables such structures to be made in high to excellent yields. One often used type of dynamic b…
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Protein Analysis Open
Protein content analysis of foods and ingredients is important for a variety of reasons. This chapter covers the instrumentation, principles, procedures, advantages, disadvantages, and applications of various protein analysis methods that …