Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues |
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Authors: | Johan F Billing |
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Institution: | Organic and Bioorganic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden |
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Abstract: | A C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues was synthesized in seven steps from tyrosine tert-butyl ester and a sugar amino acid precursor derived from D-glucosamine. An Fmoc-protected D-glucosamine derivative was oxidized at C-6 to give the sugar amino acid, which was immediately coupled to tyrosine tert-butyl ester to produce an orthogonally protected building block. This building block was subsequently elongated to the trimer via the dimer, and finally cyclized to give the C3-symmetric macrocycle. |
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Keywords: | Sugar amino acids Cyclic peptides C3 symmetry Macrocycles |
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