How cycloalkane fusion enhances the cycloaddition reactivity of dibenzocyclooctynes-Reference-Cited by-同舟云学术

How cycloalkane fusion enhances the cycloaddition reactivity of dibenzocyclooctynes

Published:2024 Issue:6 Volume:15 Page:2229-2235
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Svatunek Dennis¹²^ORCID,Murnauer Anton³,Tan Zhuoting¹,Houk K. N.¹^ORCID,Lang Kathrin³^ORCID

Affiliation:

1. Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA

2. Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria

3. Department of Chemistry and Applied Biosciences, ETH Zurich, 8093 Zurich, Switzerland

Abstract

Cis-fusion of cyclopropane to dibenzocyclooctyne (DMBO) results in high cycloaddition reactivity via enforcing a unique tub-like structure in the transition state that allows tetrazines and azides to approach DMBO from an unhindered face trajectory.

Funder

Deutsche Forschungsgemeinschaft

National Science Foundation

Austrian Science Fund

Eidgenössische Technische Hochschule Zürich

Publisher

Royal Society of Chemistry (RSC)

Link

http://pubs.rsc.org/en/content/articlepdf/2024/SC/D3SC05789E

Reference38 articles.

1. A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems

2. A Fluorogenic Probe for the Catalyst-Free Detection of Azide-Tagged Molecules

3. Selective Labeling of Living Cells by a Photo-Triggered Click Reaction

4. Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides

5. Bioorthogonal chemistry

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