87586-00-3Relevant academic research and scientific papers
Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates
Valverde, Pablo,Vendeville, Jean-Baptiste,Hollingsworth, Kristian,Mattey, Ashley P.,Keenan, Tessa,Chidwick, Harriet,Ledru, Helene,Huonnic, Kler,Huang, Kun,Light, Mark E.,Turner, Nicholas,Jiménez-Barbero, Jesús,Galan, M. Carmen,Fascione, Martin A.,Flitsch, Sabine,Turnbull, W. Bruce,Linclau, Bruno
, p. 6408 - 6411 (2020)
The first synthesis of 3-deoxy-3-fluoro-l-fucose is presented, which employs ad- tol-sugar translation strategy, and involves an enzymatic oxidation of 3-deoxy-3-fluoro-l-fucitol. Enzymatic activation (FKP) and glycosylation using an α-1,2 and an α-1,3 fu
Synthesis of UDP-4-deoxy-4-fluoroglucose and UDP-4-deoxy-4-fluorogalactose and their interactions with enzymes of nucleotide sugar metabolism
Chapeau,Frey
, p. 6994 - 6998 (2007/10/02)
Fluorinated carbohydrates can be used as probes of enzymatic active sites. We report the synthesis of 4-deoxy-4-fluoro-α-D-galactose-1-phosphate and the substrate analogues of UDP-galactose, UDP4-deoxy-4-fluoro-α-D-galactose (UDP-FGal), and of UDP-glucose, UDP-4-deoxy-4-fluoro-α-D-glucose (UDP-FGlc), which may be useful in analyzing the binding properties of enzymes that utilize nucleotide sugars as substrates. As a first step in this study, we determine the kinetic and inhibition parameters for UDP-FGal and UDP-FGlc interacting with UDP-glucose dehydrogenase and UDP-galactose 4-epimerase. UDP-FGlc is a substrate for bovine liver UDP-glucose dehydrogenase: K(m) = 30.2 ± 4.5 μM slightly higher than the value 9.6 ± 0.7 μM for UDP-glucose, and V(m)(UDP-FGlc) = 0.46V(mUDP-Glc). UDP-FGal is not a substrate for UDP-glucose dehydrogenase but is a competitive inhibitor with respect to UDP-glucose (K(i) = 19.9 ± 6.6 μM). These analogs also bind to UDP-galactose 4-epimerase from E. coli with dissociation constants K(d) of 1.4 and 1.1 mM for UDP-FGlc and UDP-FGal, respectively.
Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides.
Somawardhana,Brunngraber
, p. 51 - 60 (2007/10/02)
Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. Methyl alpha-D-glycopyranosides produced 6-deoxy-6-fluoro- and 4,6-dideoxy-4,6-difluor
