11002-83-8Relevant articles and documents
Characterization of rhodosaminyl transfer by the AknS/AknT glycosylation complex and its use in reconstituting the biosynthetic pathway of aclacinomycin A
Leimkuhler, Catherine,Fridman, Micha,Lupoli, Tania,Walker, Suzanne,Walsh, Christopher T.,Kahne, Daniel
, p. 10546 - 10550 (2007)
The tetracyclic core of anthracycline natural products with antitumor activity such as aclacinomycin A are tailored during biosynthesis by regioselective glycosylation. We report the first synthesis of TDP-L-rhodosamine and demonstrate that the glycosyltransferase AknS transfers L-rhodosamine to the aglycone to initiate construction of the side-chain trisaccharide. The partner protein AknT accelerates AknS turnover rate for L-rhodosamine transfer by 200-fold. AknT does not affect the Km but rather affects the kcat. Using these data, we propose that AknT causes a conformational change in AknS that stabilizes the transition state and ultimately enhances transfer. When the subsequent glycosyltransferase AknK and its substrate TDP-L-fucose are also added to the aglycone, the disaccharide and low levels of a fully reconstituted trisaccharide form of aclacinomycin are observed.
Practical Total Synthesis of (+/-)-Aklavinone and Total Synthesis of Aklavin
Pearlman, B. A.,McNamara, J. M.,Hasan, I.,Hatakeyama, S.,Sekizaki, H.,Kishi, Y.
, p. 4248 - 4251 (2007/10/02)
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