A family of macrocyclic antibiotics with a mixed peptide–peptoid ß-hairpin backbone conformation

Sasalu C. Shankaramma; Kerstin Moehle; Sonya James; Jan W. Vrijbloed; Daniel Obrecht; John A. Robinson

doi:10.1039/B304310J

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A family of macrocyclic antibiotics with a mixed peptide–peptoid ß-hairpin backbone conformation†

Sasalu C. Shankaramma,^a Kerstin Moehle,^a Sonya James,^a Jan W. Vrijbloed,^b Daniel Obrecht^b and John A. Robinson*^a

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* Corresponding authors

^a Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland

^b Polyphor AG, Gewerbestrasse 14, 4123 Allschwil, Switzerland

Abstract

Macrocyclic peptidomimetics having a mixed peptide–peptoid backbone have been synthesized and shown to possess antibiotic activity against Gram-positive and -negative bacteria with a low hemolytic activity against human erythrocytes; one is shown to adopt a regular ß-hairpin conformation by NMR in aqueous solution.

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Supplementary files

¹H-NMR (600 MHz) chemical shifts; ³ J coupling constants; upper distance restraints derived from integration of ROESY cross-peak volumes for the mimetic 6, as well as average backbone torsion angles φ and ψ with standard deviation found in 15 NMR structures of the mimetic 6 as shown in Fig. 1; and CD spectra for 5, 6 and 7 PDF (1230K)

Article information

DOI: https://doi.org/10.1039/B304310J
Article type: Communication
Submitted: 17 Apr 2003
Accepted: 03 Jun 2003
First published: 20 Jun 2003

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Chem. Commun., 2003, 1842-1843

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A family of macrocyclic antibiotics with a mixed peptide–peptoid ß-hairpin backbone conformation

S. C. Shankaramma, K. Moehle, S. James, J. W. Vrijbloed, D. Obrecht and J. A. Robinson, Chem. Commun., 2003, 1842 DOI: 10.1039/B304310J

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Chemical Communications

A family of macrocyclic antibiotics with a mixed peptide–peptoid ß-hairpin backbone conformation†

Abstract

Supplementary files

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A family of macrocyclic antibiotics with a mixed peptide–peptoid ß-hairpin backbone conformation

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