Novel conformationally-constrained β-peptides characterized by 1H NMR chemical shifts

Robert J. Doerksen; Bin Chen; Jing Yuan; Jeffrey D. Winkler; Michael L. Klein

doi:10.1039/B309584C

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Novel conformationally-constrained β-peptides characterized by ¹H NMR chemical shifts†

Robert J. Doerksen,^a Bin Chen,‡^a Jing Yuan,§^a Jeffrey D. Winkler*^a and Michael L. Klein*^a

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* Corresponding authors

^a Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA, USA 19104-6323
E-mail: winkler@sas.upenn.edu, klein@lrsm.upenn.edu
Fax: +1 215 573 6329
Tel: +1 215 898 0052

Abstract

For a novel family of oxanorbornene β-peptides, density functional theory computations of the three-dimensional structure and ¹H NMR chemical shifts predict that the dimer and trimer form consecutive 8-membered hydrogen-bonded ring helices, which is supported by excellent agreement with experimental solution NMR data.

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Supplementary files

Experimental procedures and spectral data for 1– 7; xyz-coordinates, relative energies, ¹H NMR chemical shifts, and H–H distances from NOESY experiments and DFT calculations for 6 and 7/8; computational methodology details DOC (418K)

Article information

DOI: https://doi.org/10.1039/B309584C
Article type: Communication
Submitted: 11 Aug 2003
Accepted: 11 Sep 2003
First published: 23 Sep 2003

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Chem. Commun., 2003, 2534-2535

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Novel conformationally-constrained β-peptides characterized by ¹H NMR chemical shifts

R. J. Doerksen, B. Chen, J. Yuan, J. D. Winkler and M. L. Klein, Chem. Commun., 2003, 2534 DOI: 10.1039/B309584C

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