Solid Phase Formylation of N-Terminus Peptides.
Formylation of amino groups is a critical reaction involved in several biological processes including post-translational modification of histones. The addition of a formyl group (CHO) to the N-terminal end of a peptide chain generates biologically active molecules. N-formyl-peptides can be produced by different methods. We performed the N-formylation of two chemotactic hexapetides, Met1-Leu2-Lys3-Leu4-Ile5-Val6 and Met1-Met2-Tyr3-Ala4-Leu5-Phe6, carrying out the reaction directly on peptidyl-resin following pre-activation of formic acid with N,N-dicyclohexylcarbodiimmide (DCC) in liquid phase. The overnight incubation at 4 °C resulted in a significant increase in production yields of formylated peptides compared to the reaction performed at room temperature. The method is consistently effective, rapid, and inexpensive. Moreover, the synthetic strategy can be applied for the formylation of all primary amines at N-terminus of peptide chains or amino groups of lysine side-chains in solid phase.
CROM, Istituto Nazionale Tumori "Fondazione G. Pascale"-IRCCS, 80131 Napoli, Italy. a.tornesello@istitutotumori.na.it.
Anna Lucia
AL
Tornesello
Inbios Srl, via Pietro Castellino 111, 80131 Napoli, Italy. info@inbios.it.
Marina
M
Sanseverino
Molecular Biology and Viral Oncology Unit, Research Department, Istituto Nazionale Tumori "Fondazione G.Pascale"-IRCCS, 80131 Napoli, Italy. fm.buonaguro@istitutotumori.na.it.
Franco Maria
FM
Buonaguro
D005561:Formates / Q000737:chemistry*; D006657:Histones / Q000737:chemistry* / Q000378:metabolism; D008239:Lysine / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D011499:Protein Processing, Post-Translational
D005561:Formates; D006657:Histones; D010455:Peptides; C030544:formic acid; D008239:Lysine
amines; formylation; peptide; solid phase synthesis