The C-glycosyltransferase UrdGT2 is unselective toward D- and L-configured nucleotide-bound rhodinoses

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Dirk Hoffmeister
  • Gerald Dräger
  • Koji Ichinose
  • Jürgen Rohr
  • Andreas Bechthold

Organisationseinheiten

Externe Organisationen

  • Albert-Ludwigs-Universität Freiburg
  • University of Wisconsin
  • University of Tokyo (UTokyo)
  • University of Kentucky
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Details

OriginalspracheEnglisch
Seiten (von - bis)4678-4679
Seitenumfang2
FachzeitschriftJournal of the American Chemical Society
Jahrgang125
Ausgabenummer16
PublikationsstatusVeröffentlicht - 23 Apr. 2003

Abstract

UrdGT2 is a D-olivosyltransferase from the metabolic pathway of urdamycin A, an angucycline antitumor and antimicrobial drug. The remarkable feature of this biocatalyst is its ability to set up C-glycosidic bonds. Using an in vivo system suitable to deliver the trideoxysugar rhodinose in both D- and L- configuration we could verify that both have been accepted as substrates and attached to the urdamycin polyketide backbone via a C-glycosidic bond. Regardless of the stereochemistry, these C-glycosides served as acceptor for a subsequent glycosylation step to yield the novel urdamycins R and S with di-rhodinosyl side chains at C-9 of the polyketide moiety.

ASJC Scopus Sachgebiete

Zitieren

The C-glycosyltransferase UrdGT2 is unselective toward D- and L-configured nucleotide-bound rhodinoses. / Hoffmeister, Dirk; Dräger, Gerald; Ichinose, Koji et al.
in: Journal of the American Chemical Society, Jahrgang 125, Nr. 16, 23.04.2003, S. 4678-4679.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Hoffmeister D, Dräger G, Ichinose K, Rohr J, Bechthold A. The C-glycosyltransferase UrdGT2 is unselective toward D- and L-configured nucleotide-bound rhodinoses. Journal of the American Chemical Society. 2003 Apr 23;125(16):4678-4679. doi: 10.1021/ja029645k
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abstract = "UrdGT2 is a D-olivosyltransferase from the metabolic pathway of urdamycin A, an angucycline antitumor and antimicrobial drug. The remarkable feature of this biocatalyst is its ability to set up C-glycosidic bonds. Using an in vivo system suitable to deliver the trideoxysugar rhodinose in both D- and L- configuration we could verify that both have been accepted as substrates and attached to the urdamycin polyketide backbone via a C-glycosidic bond. Regardless of the stereochemistry, these C-glycosides served as acceptor for a subsequent glycosylation step to yield the novel urdamycins R and S with di-rhodinosyl side chains at C-9 of the polyketide moiety.",
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AU - Ichinose, Koji

AU - Rohr, Jürgen

AU - Bechthold, Andreas

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