title: Cationic heterooligopeptides by ficain-catalyzed co-oligomerization of lysine and methionine ethylesters.
abstract: Oligopeptides are of high importance for various industrial applications, e.g. cosmetical or medical. Homooligomerizations and co-oligomerizations with anionic amino acid esters are well described but a successful synthesis of cationic heterooligopeptides has been missing so far. The present study reports the ficain-catalyzed heterooligomerizations of LysOEt with MetOEt, leading to cationic heterooligopeptides with a yield up to 49.5% (w/w). MALDI-ToF/ToF-MS analyses proved successful syntheses of cationic heterooligopeptides with a DP between 7 and 10 amino acid residues, with the enzyme exhibiting a clear preference for methionine.
authors.affiliation: Institute of Process Engineering in Life Sciences, Section II: Technical Biology, Karlsruhe Institute of Technology, Karlsruhe, Baden-Württemberg, 76131, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Andre
authors.forename: Boris
authors.initials: B
authors.lastname: Kühl
authors.forename: Gerald
authors.initials: G
authors.lastname: Brenner-Weiss
authors.forename: Christoph
authors.initials: C
authors.lastname: Syldatk
authors.forename: Jens
authors.initials: J
authors.lastname: Rudat
mesh_terms: D002412:Cations; D004952:Esters; D005361:Ficain / Q000378:metabolism*; D008239:Lysine / Q000031:analogs & derivatives* / Q000378:metabolism*; D008715:Methionine / Q000031:analogs & derivatives* / Q000378:metabolism; D009842:Oligopeptides / Q000096:biosynthesis* / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D002412:Cations; D004952:Esters; D009842:Oligopeptides; C036827:methionine ethyl ester; D008715:Methionine; D005361:Ficain; D008239:Lysine
keywords: ficain; oligopeptides; peptide synthesis; reverse proteolysis