Chemoselective Nitrile Oxide–Alkyne 1,3-Dipolar
Cycloaddition Reactions from Nitroalkane-Tethered Peptides
Posted on 2017-06-19 - 22:48
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.
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Reja, Rahi M.; Sunny, Sereena; Gopi, Hosahudya N. (2017). Chemoselective Nitrile Oxide–Alkyne 1,3-Dipolar
Cycloaddition Reactions from Nitroalkane-Tethered Peptides. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01498
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AUTHORS (3)
RR
Rahi M. Reja
SS
Sereena Sunny
HG
Hosahudya N. Gopi