title: Enzymatic synthesis of epothilone A glycosides.
abstract: Epothilones are extremely cytotoxic chemotherapeutic agents with epoxide, thiazole, and ketone groups that share equipotent kinetic similarity with taxol. The in vitro glycosylation catalyzed by uridine diphosphate glucosyltransferase (YjiC) from Bacillus licheniformis generated six novel epothilone A glycoside analouges including epothilone A 7-O-β-D-glucoside, epothilone A 7-O-β-D-galactoside, epothilone A 3,7-O-β-D-digalactoside, epothilone A 7-O-β-D-2-deoxyglucoside, epothilone A 7-O-β-L-rhamnoside, and epothilone A 7-O-β-L-fucoside. Epothilone A 7-O-β-D-glucoside was structurally elucidated by ultra-high performance liquid chromatography-photo diode array (UPLC-PDA) conjugated with high resolution quantitative time-of-flight-electrospray ionization mass spectroscopy (HR-QTOF ESI-MS/MS) supported by one-and two-dimensional nuclear magnetic resonance studies whereas other epothilone A glycosides were characterized by UPLC-PDA and HR-QTOF ESI-MS/MS analyses. The time dependent conversion study of epothilone A to epothilone A 7-O-β-D-glucoside found to be maximum (~26%) between 3 h to 5 h incubation.
authors.affiliation: Institute of Biomolecule Reconstruction (iBR), Department of Pharmaceutical Engineering, SunMoon University, Chungnam 336-708, Asan-si, Republic of Korea.
authors.forename: Prakash
authors.initials: P
authors.lastname: Parajuli
authors.affiliation: Institute of Biomolecule Reconstruction (iBR), Department of Pharmaceutical Engineering, SunMoon University, Chungnam 336-708, Asan-si, Republic of Korea.
authors.forename: Ramesh Prasad
authors.initials: RP
authors.lastname: Pandey
authors.affiliation: Institute of Biomolecule Reconstruction (iBR), Department of Pharmaceutical Engineering, SunMoon University, Chungnam 336-708, Asan-si, Republic of Korea.
authors.forename: Niranjan
authors.initials: N
authors.lastname: Koirala
authors.affiliation: Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea.
authors.forename: Yeo Joon
authors.initials: YJ
authors.lastname: Yoon
authors.affiliation: Laboratory of Molecular Biotechnology and Biomaterials, School of Chemical and Biological Engineering, Seoul National University, Seoul, Republic of Korea.
authors.forename: Byung-Gee
authors.initials: BG
authors.lastname: Kim
authors.affiliation: Institute of Biomolecule Reconstruction (iBR), Department of Pharmaceutical Engineering, SunMoon University, Chungnam 336-708, Asan-si, Republic of Korea.
authors.forename: Jae Kyung
authors.initials: JK
authors.lastname: Sohng
keywords: Bacillus licheniformis; Chemotherapeutic agent; Epothilone A glycosides; Glycosylation