Trisubstituted (E)-alkene dipeptide isosteres as beta-turn promoters in the gramicidin S cyclodecapeptide scaffold |
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| Authors: | Xiao Jingbo Weisblum Bernard Wipf Peter |
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| Institution: | Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. |
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| Abstract: | reaction: see text] A concise synthesis of a gramicidin S analogue with trisubstituted (E)-alkene dipeptide isostere (TEADI) replacements at both d-Phe-Pro positions was realized. Conformational analysis demonstrated that TEADIs can serve as type II beta-turn promoters in a cyclic scaffold and successfully mimic a proline residue. |
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