Proline editing: a divergent strategy for the synthesis of conformationally diverse peptides |
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Authors: | Thomas Krista M Naduthambi Devan Tririya Gasirat Zondlo Neal J |
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Affiliation: | Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. |
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Abstract: | [reaction: see text] 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 K(trans/cis) values, which varied from 1.5 (X = cis-fluoroproline) to 7.0 (X = trans-fluoroproline). |
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