Diversity-Oriented Syntheses of β‑Substituted α‑Amino γ‑Lactam Peptide Mimics with Constrained Backbone and Side Chain Residues

α-N-(Fmoc)­Amino-γ-lactam dipeptides with a variety of β-substituents were synthesized stereoselectively with minimal β-elimination by routes employing, respectively, Mitsunobu chemistry and cyclic sulfamidate nucleophilic ring opening from trans- and cis-β-hydroxy-α-amino-γ-lactam precursors. This...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (19), p.6126-6129
Main Authors: Geranurimi, Azade, Lubell, William D
Format: Article
Language:English
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Summary:α-N-(Fmoc)­Amino-γ-lactam dipeptides with a variety of β-substituents were synthesized stereoselectively with minimal β-elimination by routes employing, respectively, Mitsunobu chemistry and cyclic sulfamidate nucleophilic ring opening from trans- and cis-β-hydroxy-α-amino-γ-lactam precursors. This diversity-oriented method provides stereochemically pure dipeptide mimics bearing Cys, Ser, Thr, Dap, Dab, His, and other amino acid residues with constrained backbone and side chain conformations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02575