%0 Journal Article %A Reja, Rahi M. %A Sunny, Sereena %A Gopi, Hosahudya N. %D 2017 %T Chemoselective Nitrile Oxide–Alkyne 1,3-Dipolar Cycloaddition Reactions from Nitroalkane-Tethered Peptides %U https://acs.figshare.com/articles/journal_contribution/Chemoselective_Nitrile_Oxide_Alkyne_1_3-Dipolar_Cycloaddition_Reactions_from_Nitroalkane-Tethered_Peptides/5119990 %R 10.1021/acs.orglett.7b01498.s001 %2 https://ndownloader.figshare.com/files/8702731 %K nitrile oxide %K cycloaddition %K nitroalkane side chain %K azide %K peptide %K orthogonal %K Nitroalkane-Tethered Peptides Synthesis %X 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. %I ACS Publications