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Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class of strained alkynes

Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class of strained alkynes
Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class of strained alkynes

Biphenyl-fused-dioxacyclodecynes are a promising class of strained alkyne for use in Cu-free ‘click’ reactions. In this paper, a series of functionalised derivatives of this class of reagent, containing fluorescent groups, are described. Studies aimed at understanding and increasing the reactivity of the alkynes are also presented, together with an investigation of the bioconjugation of the reagents with an azide-labelled protein.

1477-0520
590-605
Forshaw, Sam
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Parker, Jeremy S.
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Scott, William T.
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Knighton, Richard C.
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Tiwari, Neelam
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Oladeji, Samson M.
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Stevens, Andrew C.
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Chew, Yean Ming
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Reber, Jami
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Clarkson, Guy J.
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Balasubramanian, Mohan K.
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Wills, Martin
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Forshaw, Sam
60fa8c3a-f84d-480b-9516-19135cb4f250
Parker, Jeremy S.
4cf85d74-85ce-4d84-af12-13aaeab8cc0f
Scott, William T.
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Knighton, Richard C.
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Tiwari, Neelam
dcbe2648-336c-4df6-93c2-85d7717a9e7b
Oladeji, Samson M.
24bed907-5c8a-4443-a5ad-a4fa6508e79e
Stevens, Andrew C.
470586cf-373d-474d-8d08-c0bc7d22de96
Chew, Yean Ming
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Reber, Jami
93324d5b-8021-421f-82ff-e06da1656842
Clarkson, Guy J.
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Balasubramanian, Mohan K.
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Wills, Martin
4529569b-d977-463d-a99f-fccec46e21a0

Forshaw, Sam, Parker, Jeremy S., Scott, William T., Knighton, Richard C., Tiwari, Neelam, Oladeji, Samson M., Stevens, Andrew C., Chew, Yean Ming, Reber, Jami, Clarkson, Guy J., Balasubramanian, Mohan K. and Wills, Martin (2023) Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class of strained alkynes. Organic and Biomolecular Chemistry, 22 (3), 590-605. (doi:10.1039/d3ob01712e).

Record type: Article

Abstract

Biphenyl-fused-dioxacyclodecynes are a promising class of strained alkyne for use in Cu-free ‘click’ reactions. In this paper, a series of functionalised derivatives of this class of reagent, containing fluorescent groups, are described. Studies aimed at understanding and increasing the reactivity of the alkynes are also presented, together with an investigation of the bioconjugation of the reagents with an azide-labelled protein.

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Accepted/In Press date: 8 December 2023
e-pub ahead of print date: 13 December 2023
Published date: 13 December 2023
Additional Information: Funding Information: we thank the EPSRC and AstraZeneca for support of SF through a National Productivity Investment Fund (NPIF) studentship and the EPSRC for support of RCK through research grant EP/M006670/1. Lijiang Song is thanked for the Mass Spectrometry analyses. The X-ray diffraction instrument was obtained through the Science City Project with support from Advantage West Midlands (AWM) and part funded by the European Regional Development Fund (ERDF). YMC and WS were supported by PhD studentships from the MRC funded Doctoral Training Partnership in Interdisciplinary Biomedical Research (grant numbers MR/R502212/1 and MR/N014294/1, respectively). SMO was supported by a Scholarship from the Commonwealth Scholarships Commission. SMO and JR were students supported by the Warwick University Analytical Sciences and Instrumentation MSc course, MKB thanks the Welcome Trust (grant 101885/C/13/Z). The authors acknowledge Dr Cleidi Zampronio and the Warwick Proteomics Research Technology Platform for Mass Spectrometry analyses. The authors thank Dr Saravanan Palani for assistance and advice with the molecular biology.

Identifiers

Local EPrints ID: 486009
URI: http://eprints.soton.ac.uk/id/eprint/486009
ISSN: 1477-0520
PURE UUID: c41f37c9-1d88-4e9a-bddb-9cf277e3ffd3
ORCID for Richard C. Knighton: ORCID iD orcid.org/0000-0002-0336-3718

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Date deposited: 05 Jan 2024 17:47
Last modified: 18 Apr 2024 02:09

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Contributors

Author: Sam Forshaw
Author: Jeremy S. Parker
Author: William T. Scott
Author: Richard C. Knighton ORCID iD
Author: Neelam Tiwari
Author: Samson M. Oladeji
Author: Andrew C. Stevens
Author: Yean Ming Chew
Author: Jami Reber
Author: Guy J. Clarkson
Author: Mohan K. Balasubramanian
Author: Martin Wills

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