Cyanoethylation of α-Amino Acids. II. Dicyanoethyl and Tricyanoethyl Derivatives²

Design of Antimicrobially Active Small Amphiphilic Peptide Dendrimers

“…Michael addition of acrylonitrile to polyamines (ethylene- or propylenediamine) and subsequent reduction of nitriles to yield amines is one of the classic routes in the dendrimer chemistry [ 31 ]. Condensation of acrylonitrile with several α-amino acids in aqueous solution in the presence of alkali salts, yielding mono-, di-, and tricyanoethyl derivatives was studied by McKinney [ 32 , 33 ].…”

Peptide Dendrimers from Natural Amino Acids

“…Thus, the high-yielding cyanoethylation [6] ± hydrogenation procedure of Meijer and co-workers [7] was adopted to make branched monomers from natural amino acids. To obviate the tedious purifications involved in many dendrimer syntheses, a liquid-phase peptide synthesis method using polyethylene glycol (PEG) as a support was employed.…”

“…The peptide dendrimers were synthesized on a poly-(ethylene glycol) monomethyl ether (MeO-PEG-OH) resin (6) [12] derivatized with glycine to form 7. Each generation of dendrimer growth comprises a deprotection, coupling, and capping reaction (i.e., 7 38 39 310, Scheme 1.…”

“…Our goal in designing a monomeric unit for the natural amino acid based dendrimers was to minimally modify the natural amino acid structures in an effort to maximize the structural resemblance to natural proteins. Thus, the high-yielding cyanoethylation [6] ± hydrogenation procedure of Meijer and co-workers [7] was adopted to make branched monomers from natural amino acids. To obviate the tedious purifications involved in many dendrimer syntheses, a liquid-phase peptide synthesis method using polyethylene glycol (PEG) as a support was employed.…”

Rapid, Scalable Assembly of Stereochemically Rich, Mono- and Bicyclic Acyl Sultams

“…6a Likewise, amino acids can be conceptually classified as ambiphilic synthons where they represent ideal starting materials as they allow for encoding stereochemical, skeletal and peripheral diversity. Furthermore, while aza-Michael addition of unprotected amino acids to acrylonitrile, 11 acrylate esters, 12 acrylaldehyde, 13 sulfones, 14 and vinylphosphoryl compounds 15 have been reported, to the best of our knowledge aza-Michael addition of unprotected amino acids to vinyl sulfonamides are absent in the literature.…”