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Enforced Folding of Unnatural Oligomers: Creating Hollow Helices with Nanosized Pores

  • Bing GongEmail author
  • Adam R. Sanford
  • Joseph S. Ferguson
Chapter
Part of the Advances in Polymer Science book series (POLYMER, volume 206)

Abstract

This article reviews the progress made during the last several years on developing folding helicaloligomers consisting of aromatic residues based on a backbone-rigidification strategy. In this approach,rigid, planar, aromatic residues are linked by planar linkers such as amide and urea functionalities. Foldinginto helical conformations is realized based on the incorporation of localized intramolecular hydrogen bondsthat limit the rotational freedom of the backbones, and through the introduction of backbone curvature bylinking the aromatic residues in a nonlinear fashion. As a result, the corresponding oligomersare forced to adopt well-defined helical conformations containing interior cavities. Changing the backbonecurvature leads to the tuning of the cavity sizes. Such enforced folding based on a “tying up”leads to stable helical backbones that are independent of side chain substitution, which offers a varietyof robust helical scaffolds for presenting functional groups. The pore-containing helices combine the featureof secondary and tertiary structures, a feature seen in few other natural or unnatural folding systems.Such an enforced folding approach should provide a simple, predictable strategy for developing a newclass of nanoporous structures with predictable dimensions.

Aromatic oligoamides Foldamer Folding Helix Nanoporous 

Abbreviations

AFM

Atomic force microscopy

CD

Circular dichroism

1D

One-dimensional

2D

Two-dimensional

DCC

Dicyclohexylcarbodiimide

DMF

N,N-Dimethylformamide

DMSO

Dimethyl sulfoxide

DNA

Deoxyribonucleic acid

EDC

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide

ESI

Electrospray ionization

GPC

Gel-permeation chromatography

HATU

1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate

IR

Infrared

MALDI

Matrix-assisted laser desorption/ionization

NMR

Nuclear magnetic resonance

NOE

Nuclear Overhauser enhancement

NOESY

Nuclear Overhauser enhancement (effect) spectroscopy

PE

Phenylene ethynylene

m-PEs

meta-Phenylene ethynylenes

TFA

Trifluoroacetyl

Tm

Melting temperature of DNA

UV

Ultraviolet

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Notes

Acknowledgments

The authors thank the current and previous Gong group members for their contributions to the research discussed in this article. Work from the authors' laboratory was supported by the National Science Foundation (CHE-0314577), the National Institutes of Health (R01GM63223), and the Office of Naval Research (N000140210519).

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Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  • Bing Gong
    • 1
    Email author
  • Adam R. Sanford
    • 1
  • Joseph S. Ferguson
    • 1
  1. 1.Department of Chemistry, University at BuffaloThe State University of New YorkBuffaloUSA

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