‘100 years of peptide synthesis’: ligation methods for peptide and protein synthesis with applications to β‐peptide assemblies
Identifieur interne : 002402 ( Istex/Curation ); précédent : 002401; suivant : 002403‘100 years of peptide synthesis’: ligation methods for peptide and protein synthesis with applications to β‐peptide assemblies
Auteurs : T. Kimmerlin [Suisse] ; D. Seebach [Suisse]Source :
- The Journal of Peptide Research [ 1397-002X ] ; 2005-02.
English descriptors
- Teeft :
- Acad, Acta, Acyl, Acyl shift, Acyl transfer, Aldehyde function, Amide, Amide bond, Amino, Amino acid, Amino acids, Anal, Analog, Angew chem, Aqueous solution, Benzyl, Calc, Chem, Chemical ligation, Chemical ligation reaction, Chim, Cleavage, Cysteine, Cysteine residues, Dawson, Deprotection, Derivatized, Ester, Experimental section, Fischer, Fmoc, Fragment, Functionality, General procedure, Helical, Helv, Hilvert, Hplc, Imine ligation, Intramolecular, Kemp, Kimmerlin, Kimmerlin seebach, Lett, Ligation, Ligation reaction, Ligation site, Linker, Methodology, Mmol, Model reaction, Native chemical ligation, Native chemical ligation methodology, Natl, Natl acad, Orthogonal, Oxime, Peptide, Peptide chemistry, Peptide fragments, Peptide synthesis, Peptide synthesis figure, Peptide thioester, Phosphate buffer, Proc, Protein synthesis, Reaction mixture, Resin, Rink amide resin, Seebach, Sequential, Sequential incorporation, Sodium thiophenate, Solid phase, Spps, Staudinger, Staudinger ligation, Staudinger reaction, Synthesis, Tetrahedron, Tetrahedron lett, Thiazolidine, Thioester, Thioesters, Thiol, Thioligation, Tion, Unprotected, Unprotected peptide fragments, Unprotected peptides.
Abstract
Abstract: A brief survey of the history of peptide chemistry from Theodore Curtius to Emil Fischer to Bruce Merrifield is first presented. The discovery and development of peptide ligation, i.e. of actual chemical synthesis of proteins are described. In the main chapter, ‘Synthesis of Proteins by Chemical Ligation’ a detailed discussion of the principles, reactivities and mechanisms involved in the various coupling strategies now applied (ligation, chemical ligation, native chemical ligation) is given. These include coupling sites with cysteine and methionine (as well as the seleno analogs), histidine, glycine and pseudo‐prolines, ‘unrestricted’ amino‐acid residues (using the Staudinger reaction), as well as solid‐phase segment coupling by thioligation of unprotected peptides. In another section, ‘Synthesis of β‐peptides by Thioligation’, couplings involving β2‐ and β3‐peptides are described (with experimental details).
Url:
DOI: 10.1111/j.1399-3011.2005.00214.x
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Seebach</name><affiliation wicri:level="1"><mods:affiliation>T. Kimmerlin and D. Seebach, Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, Swiss Federal Institute of Technology, ETH‐Hönggerberg, Zürich, Switzerland.</mods:affiliation><country xml:lang="fr">Suisse</country><wicri:regionArea>T. Kimmerlin and D. Seebach, Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, Swiss Federal Institute of Technology, ETH‐Hönggerberg, Zürich</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:8320CEE6D4E8063F4DA3A123530F3E8ABFE96792</idno><date when="2005" year="2005">2005</date><idno type="doi">10.1111/j.1399-3011.2005.00214.x</idno><idno type="url">https://api.istex.fr/ark:/67375/WNG-CW4LX11W-0/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">002402</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">002402</idno><idno type="wicri:Area/Istex/Curation">002402</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">‘100 years of peptide synthesis’: ligation methods for peptide and protein synthesis with applications to β‐peptide assemblies*</title><author><name sortKey="Kimmerlin, T" sort="Kimmerlin, T" uniqKey="Kimmerlin T" first="T." last="Kimmerlin">T. Kimmerlin</name><affiliation wicri:level="1"><mods:affiliation>T. Kimmerlin and D. Seebach, Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, Swiss Federal Institute of Technology, ETH‐Hönggerberg, Zürich, Switzerland.</mods:affiliation><country xml:lang="fr">Suisse</country><wicri:regionArea>T. Kimmerlin and D. Seebach, Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, Swiss Federal Institute of Technology, ETH‐Hönggerberg, Zürich</wicri:regionArea></affiliation></author><author><name sortKey="Seebach, D" sort="Seebach, D" uniqKey="Seebach D" first="D." last="Seebach">D. Seebach</name><affiliation wicri:level="1"><mods:affiliation>T. Kimmerlin and D. Seebach, Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, Swiss Federal Institute of Technology, ETH‐Hönggerberg, Zürich, Switzerland.</mods:affiliation><country xml:lang="fr">Suisse</country><wicri:regionArea>T. Kimmerlin and D. 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