Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor

C. M. Timmers, J. J. Turner, C. M. Ward, G. A. Van Der Marel, M. L.C.E. Kouwijzer, P. D.J. Grootenhuis, J. H. Van Boom

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Two suitably protected building blocks (11 and 33) for the preparation of amide-linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal glucuronide 21 with laminaribiosyl hemiaminal 33 and anomeric amine 11 by EDC. HOBI-catalyzed condensation and two-step conversion of the C6-OTr moiety into the corresponding carboxylate function afforded homogeneous carbopeptoid 2 in high overall yield. It was found that replacement of the acetal linkages by the more rigid amide bonds destroys the phytoalexin-elicitor activity.

Original languageEnglish (US)
Pages (from-to)920-929
Number of pages10
JournalChemistry - A European Journal
Volume3
Issue number6
DOIs
StatePublished - Jan 1 1997

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Amides
Acetals
Glucuronides
Amines
Elongation
Condensation
phytoalexins
heptaglucoside

Keywords

  • Bioorganic chemistry
  • Carbohydrates
  • Glycosides
  • Peptide bonds
  • Phytochemistry

Cite this

Timmers, C. M., Turner, J. J., Ward, C. M., Van Der Marel, G. A., Kouwijzer, M. L. C. E., Grootenhuis, P. D. J., & Van Boom, J. H. (1997). Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor. Chemistry - A European Journal, 3(6), 920-929. https://doi.org/10.1002/chem.19970030614

Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor. / Timmers, C. M.; Turner, J. J.; Ward, C. M.; Van Der Marel, G. A.; Kouwijzer, M. L.C.E.; Grootenhuis, P. D.J.; Van Boom, J. H.

In: Chemistry - A European Journal, Vol. 3, No. 6, 01.01.1997, p. 920-929.

Research output: Contribution to journalArticle

Timmers, CM, Turner, JJ, Ward, CM, Van Der Marel, GA, Kouwijzer, MLCE, Grootenhuis, PDJ & Van Boom, JH 1997, 'Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor', Chemistry - A European Journal, vol. 3, no. 6, pp. 920-929. https://doi.org/10.1002/chem.19970030614
Timmers CM, Turner JJ, Ward CM, Van Der Marel GA, Kouwijzer MLCE, Grootenhuis PDJ et al. Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor. Chemistry - A European Journal. 1997 Jan 1;3(6):920-929. https://doi.org/10.1002/chem.19970030614
Timmers, C. M. ; Turner, J. J. ; Ward, C. M. ; Van Der Marel, G. A. ; Kouwijzer, M. L.C.E. ; Grootenhuis, P. D.J. ; Van Boom, J. H. / Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor. In: Chemistry - A European Journal. 1997 ; Vol. 3, No. 6. pp. 920-929.
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