title: Programming the internal structure and stability of helical pores self-assembled from dendritic dipeptides via the protective groups of the peptide.
abstract: The synthesis of dendritic dipeptides (4-3,4-3,5)12G2-CH2-X-L-Tyr-L-Ala-OMe with X = Boc, Moc, and Ac; their self-assembly in bulk and in solution; and the structural and retrostructural analysis of their supramolecular helical porous assemblies are reported. The dimensions, structure, internal order, thermal stability of the supramolecular helical pores, and conformations of the dendron and supramolecular dendrimer are programmed by the nature of the protective groups of the dipeptide. The ability of the protective groups to program the structure of the helical pore reveals the simplest design strategy that complements the more complex strategies based on the architecture of the dendron, the stereochemistry, and the structure of the dipeptide.
authors.affiliation: Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. percec@sas.upenn.edu
authors.forename: Virgil
authors.initials: V
authors.lastname: Percec
authors.forename: Andrés E
authors.initials: AE
authors.lastname: Dulcey
authors.forename: Mihai
authors.initials: M
authors.lastname: Peterca
authors.forename: Monica
authors.initials: M
authors.lastname: Ilies
authors.forename: Monika J
authors.initials: MJ
authors.lastname: Sienkowska
authors.forename: Paul A
authors.initials: PA
authors.lastname: Heiney
mesh_terms: D000409:Alanine / Q000737:chemistry; D002942:Circular Dichroism; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D005563:Formic Acid Esters / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D011487:Protein Conformation; D013056:Spectrophotometry, Ultraviolet; D014443:Tyrosine / Q000737:chemistry
chemical_list: D004151:Dipeptides; D005563:Formic Acid Esters; D010455:Peptides; C000345:t-butyloxycarbonyl group; D014443:Tyrosine; D000409:Alanine