Solid-phase synthesis of a putative heptapeptide intermediate in vancomycin biosynthesis

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Ernst Freund and John A. Robinson


Abstract

The solid-phase synthesis was completed of the heptapeptide D-Leu-D-Tyr-L-Asn-Hpg-Hpg-L-Tyr-Dhpg, a putative intermediate in vancomycin biosynthesis, where Dhpg = (S)-3,5-dihydroxyphenylglycine and Hpg = (R)-4-hydroxyphenylglycine, using 2-chlorotrityl resin, benzyl side-chain protecting groups for the aromatic residues, and Alloc chemistry for chain elongation; the heptapeptide was obtained in 16% yield with the correct relative and absolute configuration.


References

  1. A. M. A. vanWageningen, P. N. Kirkpatrick, D. H. Williams, B. R. Harris, J. K. Kershaw, N. J. Lennard, M. Jones, S. J. M. Jones and P. J. Solenberg, Chem. Biol., 1998, 5, 155 CrossRef.
  2. P. J. Solenberg, P. Matsushima, D. R. Stack, S. C. Wilkie, R. C. Thompson and R. H. Baltz, Chem. Biol., 1997, 4, 195 CrossRef CAS.
  3. S. Pelzer, R. Sussmuth, D. Heckmann, J. Recktenwald, P. Huber, G. Jung and W. Wohlleben, Antimicrob. Agents Chemother., 1999, 43, 1565 CAS.
  4. R. D. Sussmuth, S. Pelzer, G. Nicholson, T. Walk, W. Wohlleben and G. Jung, Angew. Chem., Int. Ed., 1999, 38, 1976 CrossRef CAS.
  5. K. C. Nicolaou, C. N. C. Boddy, S. Bräse and N. Winssinger, Angew. Chem., Int. Ed., 1999, 38, 2096 CrossRef.
  6. For a review, see F. Guibé, Tetrahedron, 1998, 54, 2967 Search PubMed.
  7. K. Barlos, O. Chatzi, D. Gatos and G. Stavropoulos, Int. J. Pept. Protein Res., 1991, 37, 513 CAS.
  8. N. Thieriet, J. Alsina, E. Giralt, F. Guibé and F. Albericio, Tetrahedron Lett., 1997, 38, 7275 CrossRef CAS.
  9. H. Brückner and C. Keller-Hoehl, Chromatographia, 1990, 30, 621.
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