Difficult macrocyclizations: new strategies for synthesizing highly strained cyclic tetrapeptides |
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Authors: | Meutermans Wim D F Bourne Gregory T Golding Simon W Horton Douglas A Campitelli Marc R Craik David Scanlon Martin Smythe Mark L |
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Institution: | Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia. |
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Abstract: | reaction: see text] Cyclic tetrapeptides are an intriguing class of natural products. To synthesize highly strained cyclic tetrapeptides we developed a macrocyclization strategy that involves the inclusion of 2-hydroxy-6-nitrobenzyl (HnB) group at the N-terminus and in the "middle" of the sequence. The N-terminal auxiliary performs a ring closure/ring contraction role, and the backbone auxiliary promotes cis amide bonds to facilitate the otherwise difficult ring contraction. Following this route, the all-L cyclic tetrapeptide cyclo-Tyr-Arg-Phe-Ala] was successfully prepared. |
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