Towards peptide versions of Cram's host-guest chemistry: the synthesis of C-disubstituted glycines with binaphthol-based crowned side-chains |
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Authors: | Jean-Paul Mazaleyrat Karen WrightMaria-Vittoria Azzini Anne GaucherMichel Wakselman |
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Institution: | SIRCOB, UMR CNRS 8086, Bâtiment Lavoisier, University of Versailles, F-78000 Versailles, France |
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Abstract: | Dietherification of the hydroxy groups of various α,α-disubstituted α-amino acids or their precursors, possessing either an achiral frame derived from α-hydroxymethylserine, or a 2,2′,6,6′-tetrasubstituted biphenyl frame with only an axial chirality, or a frame with α-carbon chirality derived from α-methyl-(L)-DOPA, using (R)-2,2′-bis-(5-tosyloxy-3-oxa-1-pentyloxy)-1,1′-binaphthyl as alkylating agent, gave a new series of amino acids bearing binaphthol-based crown-ethers, as building blocks for the construction of short-chain peptide helices with topologically well-localized receptors. |
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Keywords: | binaphthol crown-ethers Cα α-disubstituted glycines modified α-amino acids |
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