The C-Glycosyltransferase UrdGT2 is unselective toward d- and l-configured nucleotide-bound rhodinoses.
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.
Hoffmeister
Dirk
D
Institute for Pharmaceutical Biology, Albert-Ludwigs-University, Stefan-Meier-Strasse 19, 79104 Freiburg, Germany.
Dräger
Gerald
G
Ichinose
Koji
K
Rohr
Jürgen
J
Bechthold
Andreas
A
D016695:Glycosyltransferases / Q000737:chemistry / Q000378:metabolism*; D009005:Monosaccharides / Q000737:chemistry / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009711:Nucleotides / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013302:Streptomyces / Q000201:enzymology; D013379:Substrate Specificity
D009005:Monosaccharides; D009711:Nucleotides; C438054:rhodinose; D016695:Glycosyltransferases