Synthesis of highly functionalized oligobenzamide proteomimetic foldamers by late stage introduction of sensitive groups

George M. Burslem; Hannah F. Kyle; Panchami Prabhakaran; Alexander L. Breeze; Thomas A. Edwards; Stuart L. Warriner; Adam Nelson; Andrew J. Wilson

doi:10.1039/c6ob00078a

Synthesis of highly functionalized oligobenzamide proteomimetic foldamers by late stage introduction of sensitive groups

George M. Burslem, Hannah F. Kyle, Panchami Prabhakaran, Alexander L. Breeze, Thomas A. Edwards, Stuart L. Warriner, Adam Nelson, Andrew J. Wilson^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

α-Helix proteomimetics represent an emerging class of ligands that can be used to inhibit an array of helix mediated protein-protein interactions. Within this class of inhibitor, aromatic oligobenzamide foldamers have been widely and successfully used. This manuscript describes alternative syntheses of these compounds that can be used to access mimetics that are challenging to synthesize using previously described methodologies, permitting access to compounds functionalized with multiple sensitive side chains and accelerated library assembly through late stage derivatisation.

Original language	English
Pages (from-to)	3782-3786
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	15
DOIs	https://doi.org/10.1039/c6ob00078a
Publication status	Published - 2016

Bibliographical note

Funding Information:
We thank AstraZeneca and EPSRC for PhD studentships (G.M.B. and H.F.K.) and the European Research Council [ERC-StG-240324, and ERC-PoC 632207] for support.

Publisher Copyright:
© The Royal Society of Chemistry 2016.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of highly functionalized oligobenzamide proteomimetic foldamers by late stage introduction of sensitive groups",

abstract = "α-Helix proteomimetics represent an emerging class of ligands that can be used to inhibit an array of helix mediated protein-protein interactions. Within this class of inhibitor, aromatic oligobenzamide foldamers have been widely and successfully used. This manuscript describes alternative syntheses of these compounds that can be used to access mimetics that are challenging to synthesize using previously described methodologies, permitting access to compounds functionalized with multiple sensitive side chains and accelerated library assembly through late stage derivatisation.",

author = "Burslem, {George M.} and Kyle, {Hannah F.} and Panchami Prabhakaran and Breeze, {Alexander L.} and Edwards, {Thomas A.} and Warriner, {Stuart L.} and Adam Nelson and Wilson, {Andrew J.}",

note = "Funding Information: We thank AstraZeneca and EPSRC for PhD studentships (G.M.B. and H.F.K.) and the European Research Council [ERC-StG-240324, and ERC-PoC 632207] for support. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

doi = "10.1039/c6ob00078a",

language = "English",

volume = "14",

pages = "3782--3786",

journal = "Organic and Biomolecular Chemistry",

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T1 - Synthesis of highly functionalized oligobenzamide proteomimetic foldamers by late stage introduction of sensitive groups

AU - Burslem, George M.

AU - Kyle, Hannah F.

AU - Prabhakaran, Panchami

AU - Breeze, Alexander L.

AU - Edwards, Thomas A.

AU - Warriner, Stuart L.

AU - Nelson, Adam

AU - Wilson, Andrew J.

N1 - Funding Information: We thank AstraZeneca and EPSRC for PhD studentships (G.M.B. and H.F.K.) and the European Research Council [ERC-StG-240324, and ERC-PoC 632207] for support. Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016

Y1 - 2016

N2 - α-Helix proteomimetics represent an emerging class of ligands that can be used to inhibit an array of helix mediated protein-protein interactions. Within this class of inhibitor, aromatic oligobenzamide foldamers have been widely and successfully used. This manuscript describes alternative syntheses of these compounds that can be used to access mimetics that are challenging to synthesize using previously described methodologies, permitting access to compounds functionalized with multiple sensitive side chains and accelerated library assembly through late stage derivatisation.

AB - α-Helix proteomimetics represent an emerging class of ligands that can be used to inhibit an array of helix mediated protein-protein interactions. Within this class of inhibitor, aromatic oligobenzamide foldamers have been widely and successfully used. This manuscript describes alternative syntheses of these compounds that can be used to access mimetics that are challenging to synthesize using previously described methodologies, permitting access to compounds functionalized with multiple sensitive side chains and accelerated library assembly through late stage derivatisation.

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DO - 10.1039/c6ob00078a

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AN - SCOPUS:84964612414

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EP - 3786

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 15

ER -

Synthesis of highly functionalized oligobenzamide proteomimetic foldamers by late stage introduction of sensitive groups

Abstract

Bibliographical note

ASJC Scopus subject areas

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