Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 103, Issue 8, Pages 2518-2523Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.0509676103
Keywords
chiral dendrons; porous supramolecular columns; protein mimics; pepticle stereochemistry
Categories
Ask authors/readers for more resources
The self-assembly of the dendritic dipeptides (4-3,4-3,5)nG2-CH2-BOC-L-Tyr-L-Ala-OMe and their achiral dendritic alcohol (4-3,43,5)nG2-CH2OH precursors, both with n = 1-16, where n represents the number of methylenic units in the alkyl groups of the dendron, are reported. All chiral dendritic dipeptides and achiral dendritic alcohols self-assemble into helical porous columns that are stable in both solution and solid state. The pore diameter (D-pore) of the columns self-assembled from dendritic dipeptides is approximate to 10 angstrom larger than that of structures assembled from dendritic alcohols. The increase of the Dpore at the transition from dendritic alcohol to dendritic dipeptide is accompanied by a decreased solid angle of the building block. This trend is in agreement with previous pore size-solid angle dependences observed with different protective groups of the dipeptide and primary structures of the dendron. However, within the series of dendritic alcohols and dendritic dipeptides with various n, the Dpore increases when the solid angle increases. The results of these investigations together with those of previous studies on the role of dipeptide stereochemistry and protective groups on this self-assembly process provide the molecular principles required to program the construction of supramolecular helical pores with diameter controlled at the A level from a single dendritic dipeptide architecture. These principles are expected to be valid for libraries of dendritic dipeptides based on dendrons and dipeptides with various primary structures.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available