title: Supramolecular PEG-co-oligo(p-benzamide)s prepared on a peptide synthesizer.
abstract: An automated synthesis protocol has been developed for the preparation of oligo(p-benzamide)s on solid support using a commercial peptide synthesizer employing a variation of standard Fmoc chemistry. Bis(trichloromethyl carbonate) in NMP was used to activate the aromatic carboxylic acids for acylation of secondary aromatic amines on solid support. N-Protected hepta(p-benzamide) was automatically prepared on solid support and manually converted to a solid supported block co-oligomer by attaching a poly(ethylene glycol) chain. Cleavage from the support could be achieved with minimal loss of the p-methoxybenzyl N-protective group. While the N-protected block co-oligomer was molecularly dissolved in nonpolar organic solvents, the N-deprotected block co-oligomer adopted a rod-coil conformation and showed strong aggregation as evidenced by gel permeation chromatography and transmission electron microscopy. Rigid rodlike aggregates could be observed in chloroform, toluene, as well as water.
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.
authors.forename: Hannah M
authors.initials: HM
authors.lastname: König
authors.forename: Tatiana
authors.initials: T
authors.lastname: Gorelik
authors.forename: Ute
authors.initials: U
authors.lastname: Kolb
authors.forename: Andreas F M
authors.initials: AF
authors.lastname: Kilbinger
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D001672:Biocompatible Materials / Q000138:chemical synthesis*; D002850:Chromatography, Gel; D009682:Magnetic Resonance Spectroscopy; D046529:Microscopy, Electron, Transmission; D008956:Models, Chemical; D010455:Peptides / Q000138:chemical synthesis*; D011092:Polyethylene Glycols / Q000737:chemistry*; D011487:Protein Conformation
chemical_list: D001549:Benzamides; D001672:Biocompatible Materials; D010455:Peptides; D011092:Polyethylene Glycols; C037689:benzamide