Design, synthesis and conformational analysis of oligobenzanilides as multi-facial alpha-helix mimetics
File(s)acs.orglett.9b01115.pdf (2.02 MB)
Published version
Author(s)
Flack, T
Romain, C
White, A
Haycock, P
Barnard, A
Type
Journal Article
Abstract
The design, synthesis, and conformational analysis of an oligobenzanilide helix mimetic scaffold capable of simultaneous mimicry of two faces of an α-helix is reported. The synthetic methodology provides access to diverse monomer building blocks amenable to solid-phase assembly in just four synthetic steps. The conformational flexibility of model dimers was investigated using a combination of solid and solution state methodologies supplemented with DFT calculations. The lack of noncovalent constraints allows for significant conformational plasticity in the scaffold, thus permitting it to successfully mimic residues i, i+2, i+4, i+6, i +7, and i+9 of a canonical α-helix.
Date Issued
2019-06-21
Date Acceptance
2019-06-01
ISSN
1523-7052
Publisher
American Chemical Society
Start Page
4433
End Page
4438
Journal / Book Title
Organic Letters
Volume
21
Issue
12
Copyright Statement
© 2019 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY)
License, which permits unrestricted use, distribution and reproduction in any medium,
provided the author and source are cited.
License, which permits unrestricted use, distribution and reproduction in any medium,
provided the author and source are cited.
Sponsor
Wellcome Trust
Identifier
https://pubs.acs.org/doi/10.1021/acs.orglett.9b01115
Grant Number
105603/Z/14/Z
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
PROTEIN-PROTEIN INTERACTIONS
EXPLORING KEY ORIENTATIONS
SMALL-MOLECULE INHIBITORS
ROTATION
INTERFACES
AMIDE
03 Chemical Sciences
Organic Chemistry
Publication Status
Published
Date Publish Online
2019-06-12