Department of Chemistry, Indian Institute of Science Education and Research , Dr. Homi Bhabha Road, Pune 411 008, India.
Org Lett. 2017 Jul 7;19(13):3572-3575. doi: 10.1021/acs.orglett.7b01498. Epub 2017 Jun 20.
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.
报道了一种新型含硝基烷侧链氨基酸的合成和掺入、硝基烷侧链原位转化为硝酮氧化物，以及原位生成的硝酮氧化物与不同炔烃之间的化学选择性 1,3-偶极环加成反应。发现硝基烷介导的硝酮氧化物-炔烃环加成反应与铜（I）催化的叠氮化物-炔烃环加成反应是正交的。正交的硝酮氧化物-炔烃和叠氮化物-炔烃环加成反应的组合可以分别探索用于在肽骨架上定制不同的 1,2,3-三唑和 3,5-异恶唑。
