Synthesis of enaminone-based vinylogous peptides was written by Senica, Luka;Groselj, Uros;Kasunic, Marta;Kocar, Drago;Stanovnik, Branko;Svete, Jurij. And the article was included in European Journal of Organic Chemistry in 2014.Recommanded Product: 87694-53-9 This article mentions the following:
Vinylogous peptides 3 [E-I or Z-I (Boc = tert-butoxycarbonyl; R1 = H, Me, Bn; AA = amino acid or peptide)] with a vinyl fragment inserted into the peptide C-N bond were prepared from ynones (II) (R1 = H, Me, Bn) and enaminones (E-III) (R1 = H, Me, Bn) that are easily available from Boc-protected α-amino acids. Coupling at the C terminus was achieved by 1,4-addition of amino esters to the C C bond in II or by substitution of the NMe2 group in III to give N-terminal vinylogous peptides. Coupling at the N terminus of I and III in contrast, required temporary protection of the acidolytically labile enamino moiety. Cyclization of II or III with hydroxylamine, removal of the Boc group with HBr-AcOH, acylation of free amine hydrobromides (IV) (R1 = H, Me, Bn) with BocGlyOH, and hydrogenolytic deprotection of the enamino moiety in the presence of GlyOMe led to tripeptides with vinylogous amide as the central building block. Thus, the present method enables incorporation of vinylogous amide (building blocks) BBs into oligopeptides. However, the preparation of oligomers with consecutive vinylogous BBs represents the next synthetic challenge to be met. These preliminary results clearly indicate the viability of this synthetic approach, which enables the incorporation of vinylogous amides into a peptide chain. Vinylogous peptides might be interesting or even useful for various applications, for example, in medicinal chem., chem. biol., and in materials science. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Recommanded Product: 87694-53-9).
(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Recommanded Product: 87694-53-9
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics