Supramolecular PEG-co-oligo(p-benzamide)s prepared on a peptide synthesizer.
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.
König
Hannah M
HM
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.
Gorelik
Tatiana
T
Kolb
Ute
U
Kilbinger
Andreas F M
AF
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
D001549:Benzamides; D001672:Biocompatible Materials; D010455:Peptides; D011092:Polyethylene Glycols; C037689:benzamide