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Double-sided a-helix mimetics

Double-sided a-helix mimetics
Double-sided a-helix mimetics
The design and synthesis of substituted bis- and tris-benzamides is reported in which the projection of side-chain residues on both sides of an ?-helix is reproduced. The scaffold is conformationally constrained by a series of intramolecular hydrogen bonds, allowing for spatial and angular mimicry of the i, i+2, i+4 and i+6 side-chains in the case of the bis-benzamide, and may be extended to higher-order oligomers.
0040-4020
4501-4505
Thompson, Sam
99b7e34e-fe24-401c-b7b0-64e56cbbbcb1
Vallinayagam, Ramakrishnan
3fb93055-78c4-4784-973c-6559812a02e2
Adler, Marc J.
f54d3656-b0dc-476e-a37d-7ee2d00d5acf
Scott, Richard T.W.
b7c85907-eec6-46da-b268-b21c6f5ecb09
Hamilton, Andrew D.
048a6c75-91bf-4555-ab12-ce885eee65dd
Thompson, Sam
99b7e34e-fe24-401c-b7b0-64e56cbbbcb1
Vallinayagam, Ramakrishnan
3fb93055-78c4-4784-973c-6559812a02e2
Adler, Marc J.
f54d3656-b0dc-476e-a37d-7ee2d00d5acf
Scott, Richard T.W.
b7c85907-eec6-46da-b268-b21c6f5ecb09
Hamilton, Andrew D.
048a6c75-91bf-4555-ab12-ce885eee65dd

Thompson, Sam, Vallinayagam, Ramakrishnan, Adler, Marc J., Scott, Richard T.W. and Hamilton, Andrew D. (2012) Double-sided a-helix mimetics. [in special issue: Chemistry of Foldamers] Tetrahedron, 68 (23), 4501-4505. (doi:10.1016/j.tet.2011.11.010).

Record type: Article

Abstract

The design and synthesis of substituted bis- and tris-benzamides is reported in which the projection of side-chain residues on both sides of an ?-helix is reproduced. The scaffold is conformationally constrained by a series of intramolecular hydrogen bonds, allowing for spatial and angular mimicry of the i, i+2, i+4 and i+6 side-chains in the case of the bis-benzamide, and may be extended to higher-order oligomers.

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Accepted/In Press date: 4 November 2011
e-pub ahead of print date: 12 November 2011
Published date: 10 June 2012
Organisations: Chemistry

Identifiers

Local EPrints ID: 403612
URI: http://eprints.soton.ac.uk/id/eprint/403612
ISSN: 0040-4020
PURE UUID: 94559def-5c47-42c5-acc5-5d3442f7369a
ORCID for Sam Thompson: ORCID iD orcid.org/0000-0001-6267-5693

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Date deposited: 07 Dec 2016 13:34
Last modified: 03 Dec 2019 01:32

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Contributors

Author: Sam Thompson ORCID iD
Author: Ramakrishnan Vallinayagam
Author: Marc J. Adler
Author: Richard T.W. Scott
Author: Andrew D. Hamilton

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