St-Cyr, D. J., Jamieson, A. G. and Lubell, W. D. (2010) α-Amino-β-hydroxy-γ-lactam for constraining peptide Ser and Thr residue conformation. Organic Letters, 12(8), pp. 1652-1655. (doi: 10.1021/ol1000582)
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Abstract
α-Amino-β-hydroxy-γ-lactam 1 is a peptide mimic in which the Ser/Thr residue ω-, ψ-, and χ-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of β-hydroxy-γ-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Jamieson, Professor Andrew |
| Authors: | St-Cyr, D. J., Jamieson, A. G., and Lubell, W. D. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Organic Letters |
| Publisher: | American Chemical Society |
| ISSN: | 1523-7060 |
| ISSN (Online): | 1523-7052 |
| Published Online: | 12 March 2010 |
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