ol7b01498_si_002.cif (2.47 MB)
Chemoselective Nitrile Oxide–Alkyne 1,3-Dipolar Cycloaddition Reactions from Nitroalkane-Tethered Peptides
dataset
posted on 2017-06-19, 22:48 authored by Rahi M. Reja, Sereena Sunny, Hosahudya N. GopiSynthesis 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.