Function of glycosyltransferase genes involved in urdamycin A biosynthesis

Abstract

Analysis of glycosyltransferase genes of the urdamycin biosynthetic gene cluster led to an unambiguous assignment of each glycosyltransferase to a certain biosynthetic saccharide attachment step.

Identification of the Function of Gene lndM2 Encoding a Bifunctional Oxygenase-Reductase Involved in the Biosynthesis of the Antitumor Antibiotic Landomycin E by Streptomyces globisporus 1912 Supports the Originally Assigned Structure for Landomycinone

“…8, 21 We could not detect any changes in the production spectrum of S. fradiae and its mutant strains upon expressing either lndM2 or lanM2. Thus the LanM2/LndM2 protein recognizes neither urdamycin A nor any of its intermediates as a substrate.…”

In vitro characterization of IroB, a pathogen-associated C -glycosyltransferase

“…Very few examples of C-glycoside-bearing natural products have been described; among these are the maysinfamily maize flavones (36) and the polyketides granaticin (37), simocyclinone D8 (38), and the angucycline antibiotics (27,(39)(40)(41). All of the C-Gtfs must generate a carbon nucleophile to attack C1Ј of the glycosyl moiety of the donor cosubstrate NDP-hexose (Fig.…”

On the Acceptor Substrate of C‐Glycosyltransferase UrdGT2: Three Prejadomycin C‐Glycosides from an Engineered Mutant of Streptomyces globisporus 1912 ΔlndE(urdGT2)

“…[1][2][3][4][5][6] The landomycins are closely related to the urdamycins (e.g., urdamycin A (5)). [7][8][9] Both possess a polyketide-derived angucyclinone core and sugar moieties consisting of D-olivose and L-rhodinose building blocks. Major structural differences were found in the assembly of the sugar moieties and in the oxygenation pattern of the polyketide core moiety.…”

“…Major structural differences were found in the assembly of the sugar moieties and in the oxygenation pattern of the polyketide core moiety. [1,4,5,[10][11][12] The availability of the biosynthetic gene clusters of urdamycins and landomycins [7,[13][14][15][16][17] made it possible to track down the genes encoding the biosynthetic enzymes responsible for the unique structural features of the two types of compounds, which are also responsible for the significant variations in the biological activities of these related anti-cancer drugs. [18] The overall structural and biosynthetic similarity between these two closely related sets of antibiotics allowed several successful combinatorial, biosynthetic gene-combination experiments, leading to new hybrid molecules.…”