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Proline Editing: A Divergent Strategy for the Synthesis of Conformationally Diverse Peptides

2005; American Chemical Society; Volume: 7; Issue: 12 Linguagem: Inglês

10.1021/ol0506720

1523-7060

Krista Thomas, Devan Naduthambi, Gasirat Tririya, Neal J. Zondlo,

RNA and protein synthesis mechanisms

Strong conformational biases in peptides and proteins can be achieved with 4-substituted proline residues (cis-, trans-, or disubstituted fluoroproline or hydroxyproline). The practical, divergent synthesis of peptides containing these residues, via postsynthetic modification of a peptide containing an internal trans-hydroxyproline residue, is described. Significant differences in the conformations of the peptides Ac-TYXN-NH2 were observed, including Ktrans/cis values, which varied from 1.5 (X = cis-fluoroproline) to 7.0 (X = trans-fluoroproline).