Organic Letters
Organic Letters
5 years ago

Chemoselective Nitrile Oxide–Alkyne 1,3-Dipolar Cycloaddition Reactions from Nitroalkane-Tethered Peptides

Chemoselective Nitrile Oxide–Alkyne 1,3-Dipolar Cycloaddition Reactions from Nitroalkane-Tethered Peptides
Sereena Sunny, Hosahudya N. Gopi, Rahi M. Reja
Synthesis and incorporation of a new amino acid with a nitroalkane side chain into peptides, in situ transformation of a nitroalkane side chain into nitrile oxide, and chemoselective 1,3-dipolar cycloaddition reactions between in situ generated nitrile oxide and different alkynes are reported. The nitroalkane-mediated nitrile oxide–alkyne cycloaddition was found to be orthogonal to the copper(I)-catalyzed azide–alkyne cycloaddition reaction. The combination of orthogonal nitrile oxide–alkyne and azide–alkyne cycloaddition reactions can be explored to tailor different 1,2,3-triazole and 3,5-isoxazoles, respectively, on the peptide backbone.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01498

DOI: 10.1021/acs.orglett.7b01498

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.