Coupling of two amino acids in solution. The unprotected amine of one reacts with the unprotected carboxylic acid group of the other to form a peptide bond. In this example, the second reactive group (amine/acid) in each of the starting materials bears a protecting group.
In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains.[1] Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus).[2] Protein biosynthesis (long peptides) in living organisms occurs in the opposite direction.
The chemical synthesis of peptides can be carried out using classical solution-phase techniques, although these have been replaced in most research and development settings by solid-phase methods (see below).[3] Solution-phase synthesis retains its usefulness in large-scale production of peptides for industrial purposes moreover.
Chemical synthesis facilitates the production of peptides that are difficult to express in bacteria, the incorporation of unnatural amino acids, peptide/protein backbone modification, and the synthesis of D-proteins, which consist of D-amino acids.
^Isidro-Llobet A, Alvarez M, Albericio F (June 2009). "Amino acid-protecting groups". Chemical Reviews. 109 (6): 2455–2504. doi:10.1021/cr800323s. hdl:2445/69570. PMID 19364121. S2CID 90409290.
^Chan WC, White PD (2000). Fmoc Solid Phase Peptide Synthesis: A Practical Approach. Oxford, UK: OUP. ISBN 978-0-19-963724-9.
^Jaradat DM (January 2018). "Thirteen decades of peptide synthesis: key developments in solid phase peptide synthesis and amide bond formation utilized in peptide ligation". Amino Acids. 50 (1): 39–68. doi:10.1007/s00726-017-2516-0. PMID 29185032. S2CID 3680612.
chemistry, peptidesynthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds....
Bailey peptidesynthesis is a name reaction in organic chemistry developed 1949 by J. L. Bailey. It is a method for the synthesis of a peptide from α-amino...
Nonribosomal peptides (NRP) are a class of peptide secondary metabolites, usually produced by microorganisms like bacteria and fungi. Nonribosomal peptides are...
constituents Peptidesynthesis, the biochemical synthesis of peptides using amino acids Protein biosynthesis, the multi-step biochemical synthesis of proteins...
Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides that have...
Rockefeller University. Her research considers peptidesynthesis. She discovered the glucagon-like peptide-1 and uncovered its role in glucose metabolism...
single-enantiomer chiral molecules and to improve the efficiency of peptidesynthesis. Automated peptidesynthesis involves the condensation of the amino group of protected...
To make protein-sized polypeptide chains with the small peptide fragments made by synthesis, chemical biologists can use the process of native chemical...
produce peptides at sufficient concentrations. Thus, mineral surface catalysis, while important, is not sufficient alone for peptidesynthesis. Many prebiotically...
software. Combinatorial chemistry can be used for the synthesis of small molecules and for peptides. Strategies that allow identification of useful components...
Nobel Prize in Chemistry in 1984 for the invention of solid phase peptidesynthesis. He was born in Fort Worth, Texas, on 15 July 1921, the only son of...
arise from post-translational modification or during nonribosomal peptidesynthesis. The carbon atom next to the carboxyl group is called the α–carbon...
Protein biosynthesis (or protein synthesis) is a core biological process, occurring inside cells, balancing the loss of cellular proteins (via degradation...
scavenger in peptidesynthesis. It can also act as a mild reducing agent. In peptidesynthesis, TIPS is used as a scavenger for peptide groups being removed...
and PeptideSynthesis, 2nd edn., Oxford University Press, 2002 Wuts, P. G. M.; Greene, T.W. (2006). Greene's Protective Groups in Organic Synthesis. NY:...
dehydration synthesis. Some peptides, like alpha-amanitin, are called ribosomal peptides as they are made by ribosomes, but many are nonribosomal peptides as they...
additional oxygens attached. The chemical is a useful reagent for peptidesynthesis reactions, where it activates the carboxylic acid partner for subsequent...
often used for the coupling of amino acids for peptidesynthesis and as a reagent in organic synthesis. CDI can be prepared straightforwardly by the reaction...
Schematic diagram of a solid-state peptidesynthesis with orthogonal protecting groups X and Y Fmoc solid state peptidesynthesis with orthogonal protecting groups...
additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptidesynthesis. It acts as a neutralizing reagent for the basicity or nucleophilicity...
Custom peptidesynthesis is the commercial production of peptides for use in biochemistry, biology, biotechnology, pharmacology and molecular medicine...
strategy a peptide chain and glycan residue are first synthesis separately. Then the glycan is glycosylated onto a specific residue of the peptide chain....
method of peptidesynthesis he developed with Max Bergmann. This was the first successful method of controlled peptide chemical synthesis and for twenty...
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