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Chemoselectivity of Tertiary Azides in Strain-Promoted Alkyne-Azide Cycloadditions.


ABSTRACT: The strain-promoted alkyne-azide cycloaddition (SPAAC) is the most commonly employed bioorthogonal reaction with applications in a broad range of fields. Over the years, several different cyclooctyne derivatives have been developed and investigated in regard to their reactivity in SPAAC reactions with azides. However, only a few studies examined the influence of structurally diverse azides on reaction kinetics. Herein, we report our investigations of the reactivity of primary, secondary, and tertiary azides with the cyclooctynes BCN and ADIBO applying experimental and computational methods. All azides show similar reaction rates with the sterically non-demanding cyclooctyne BCN. However, due to the increased steric demand of the dibenzocyclooctyne ADIBO, the reactivity of tertiary azides drops by several orders of magnitude in comparison to primary and secondary azides. We show that this chemoselective behavior of tertiary azides can be exploited to achieve semiorthogonal dual-labeling without the need for any catalyst using SPAAC exclusively.

SUBMITTER: Svatunek D 

PROVIDER: S-EPMC6391941 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Chemoselectivity of Tertiary Azides in Strain-Promoted Alkyne-Azide Cycloadditions.

Svatunek Dennis D   Houszka Nicole N   Hamlin Trevor A TA   Bickelhaupt F Matthias FM   Mikula Hannes H  

Chemistry (Weinheim an der Bergstrasse, Germany) 20181206 3


The strain-promoted alkyne-azide cycloaddition (SPAAC) is the most commonly employed bioorthogonal reaction with applications in a broad range of fields. Over the years, several different cyclooctyne derivatives have been developed and investigated in regard to their reactivity in SPAAC reactions with azides. However, only a few studies examined the influence of structurally diverse azides on reaction kinetics. Herein, we report our investigations of the reactivity of primary, secondary, and ter  ...[more]

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