α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation

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 ac...

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Veröffentlicht in:	Organic letters 2010-04, Vol.12 (8), p.1652-1655
Hauptverfasser:	St-Cyr, Daniel J, Jamieson, Andrew G, Lubell, William D
Format:	Artikel
Sprache:	eng
Schlagworte:	Lactams - chemistry Molecular Conformation Peptides - chemistry Serine - chemistry Threonine - chemistry
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creator	St-Cyr, Daniel J Jamieson, Andrew G Lubell, William D
description	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.
doi_str_mv	10.1021/ol1000582
format	Article
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Lett</addtitle><description>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. 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subjects	Lactams - chemistry Molecular Conformation Peptides - chemistry Serine - chemistry Threonine - chemistry
title	α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation
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