Trisubstituted (E)-alkene dipeptide isosteres as beta-turn promoters in the gramicidin S cyclodecapeptide scaffold.
[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.
Xiao
Jingbo
J
Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Weisblum
Bernard
B
Wipf
Peter
P
D000475:Alkenes / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D006096:Gramicidin / Q000138:chemical synthesis / Q000737:chemistry*; D018716:Molecular Mimicry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D011487:Protein Conformation; D017433:Protein Structure, Secondary
D000475:Alkenes; D004151:Dipeptides; D010456:Peptides, Cyclic; D006096:Gramicidin; D011392:Proline