Incorporating NOE-Derived Distances in Conformer Generation of Cyclic Peptides with Distance Geometry


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Date

2022-02-14

Publication Type

Journal Article

ETH Bibliography

yes

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Abstract

Nuclear magnetic resonance (NMR) data from NOESY (nuclear Overhauser enhancement spectroscopy) and ROESY (rotating frame Overhauser enhancement spectroscopy) experiments can easily be combined with distance geometry (DG) based conformer generators by modifying the molecular distance bounds matrix. In this work, we extend the modern DG based conformer generator ETKDG, which has been shown to reproduce experimental crystal structures from small molecules to large macrocycles well, to include NOE-derived interproton distances. In noeETKDG, the experimentally derived interproton distances are incorporated into the distance bounds matrix as loose upper (or lower) bounds to generate large conformer sets. Various subselection techniques can subsequently be applied to yield a conformer bundle that best reproduces the NOE data. The approach is benchmarked using a set of 24 (mostly) cyclic peptides for which NOE-derived distances as well as reference solution structures obtained by other software are available. With respect to other packages currently available, the advantages of noeETKDG are its speed and that no prior force-field parametrization is required, which is especially useful for peptides with unnatural amino acids. The resulting conformer bundles can be further processed with the use of structural refinement techniques to improve the modeling of the intramolecular nonbonded interactions. The noeETKDG code is released as a fully open-source software package available at www.github.com/rinikerlab/customETKDG.

Publication status

published

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Volume

62 (3)

Pages / Article No.

472 - 485

Publisher

American Chemical Society

Event

Edition / version

Methods

Software

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Date created

Subject

Organisational unit

09458 - Riniker, Sereina Z. / Riniker, Sereina Z. check_circle

Notes

Funding

178762 - Passive Membrane-Permeability Prediction for Peptides and Peptidomimetics Using Computational Methods (SNF)

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