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

Published on 2017-06-19T22:48:57Z (GMT) by
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.

Cite this collection

Reja, Rahi M.; Sunny, Sereena; Gopi, Hosahudya N. (2017): Chemoselective Nitrile Oxide–Alkyne 1,3-Dipolar

Cycloaddition Reactions from Nitroalkane-Tethered Peptides. ACS Publications.

https://doi.org/10.1021/acs.orglett.7b01498

Retrieved: 01:46, Jun 26, 2017 (GMT)