1614240-40-2Relevant academic research and scientific papers
Synthesis of enaminone-based vinylogous peptides
Senica, Luka,Groselj, Uros,Kasunic, Marta,Kocar, Drago,Stanovnik, Branko,Svete, Jurij
supporting information, p. 3067 - 3071 (2014/06/09)
Vinylogous peptides 3 with a vinyl fragment inserted into the peptide C-N bond were prepared from ynones 6 and enaminones 7 that are easily available from Boc-protected α-amino acids 4. Coupling at the C terminus was achieved by 1,4-addition of amino esters 5 to the C≡C bond in 6 or by substitution of the NMe2 group in 7 to give N-terminal vinylogues 3a-p. Coupling at the N terminus of 3 and 7, in contrast, required temporary protection of the acidolytically labile enamino moiety. Thus, cyclization of 6 or 7 with hydroxylamine, removal of the Boc group with HBr-AcOH, acylation of free amine 10 with BocGlyOH (4a), and hydrogenolytic deprotection of the enamino moiety in the presence of GlyOMe (5a) led to tripeptides 3q-s with vinylogous amide as the central building block. Copyright
