A facile preparation of functional cycloalkynes via an azide-to-cycloalkyne switching approach.

Chem Commun (Camb)

Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.

Published: March 2019

AI Article Synopsis

  • - A new, easy method has been created to prepare different functional cycloalkynes, including those integrated with proteins, using azides as starting materials
  • - The process involves treating diynes with a copper salt to selectively react terminal alkynes with azides
  • - Additionally, a more reactive strained alkyne is temporarily protected from reacting by forming a complex with copper, allowing for better control in the synthesis

Article Abstract

A facile method for preparing various functional cycloalkynes, including proteins incorporated with a cycloalkyne moiety, from the corresponding azides is developed. Treatment of diynes bearing strained and terminal alkyne moieties with a copper salt enabled terminal alkyne-selective click conjugation with azides, whereas a more azidophilic strained alkyne moiety was transiently protected from the click reaction via complexation with copper.

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Source
http://dx.doi.org/10.1039/c9cc01113gDOI Listing

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