An expedient enzymatic route to isomeric 2-, 3- and 6-monodeoxy-monofluoro-maltose derivatives

Flux through Trehalose Synthase Flows from Trehalose to the Alpha Anomer of Maltose in Mycobacteria

“…Since Mycobacterium tuberculosis has a trehalose transporter (Kalscheuer et al., 2010a) and TreS has been reported to utilize 2-fluoro-2-deoxymaltose as a substrate (Zhang et al., 2011), the ability of TreS to convert 2-, 3-, and 6-deoxyfluoromaltose analogs (Tantanarat et al., 2012) was monitored using 19 F-NMR spectroscopy (Figure 4). The 2-deoxy-2-fluoro and 6-deoxy-6-fluoro compounds were converted to the corresponding deoxyfluorotrehalose analogs ∼2-fold and ∼180-fold less efficiently than the normal substrate (Figures 4A and 4C).…”

Enzymatic Synthesis of Acarviosyl-maltooligosaccharides Using Disproportionating Enzyme 1

“…Tantanarat and co-workers used GH family 77 enzymes, including DPE1, to synthesize several fluoro sugars, which are tracers used in fluorine NMR and should contribute to research on glycoside hydrolases. 25) Hence, disproportionating enzymes can be useful to synthesize valuable carbohydrates with high productivity. Synthesized ACn might function as an effective inhibitor of exo-type -glucoside-active enzymes.…”

Control of Transposon-mediated Activation of theglpFKOperon ofEscherichia coliby two DNA binding Proteins

“…Since a reduction in cAMP promotes IS 5 insertion in the glpFK activating site, we sought to determine whether environmental conditions that could lead to a reduction in cAMP concentrations could elevate IS 5 insertion into the glpFK promoter. Non-metabolizable glucose analogues, such as 2-deoxyglucose (2DG) and α-methylglucoside (αMG), (He and Liu, 2002, Holst and Williamson, 2004, Kumar et al, 2013, Moller, 2010, Tantanarat et al, 2012, Saier and Ballou, 1968, Xi et al, 2014) are known to lower cytoplasmic cAMP levels by inhibiting adenylate cyclase activity (Gabor et al, 2011, Gershanovich, 2003, Saier et al, 1996, Vastermark and Saier, 2014). These analogues also strongly inhibit growth on glycerol, at least in part due to inhibition of both cytoplasmic cAMP production by adenylate cyclase, and of cytoplasmic glycerol-3-phosphate (substrate/inducer) production by glycerol kinase (Kuroda et al, 2001, Peterkofsky et al, 2001, Schlegel et al, 2002, Saier and Reizer, 1994).…”

“…In fact, numerous toxic and non-metabolizable sugar analogues are synthesized by microorganisms, plants, fungi and man. They include deoxy sugars such as 2-deoxyglucose, methylated sugars, such as 3- and 6-0 methyl glucose, fluoro sugars and a variety of α- and β-glycosides such as methyl α-glucoside (He and Liu, 2002, Holst and Williamson, 2004, Kumar et al, 2013, Moller, 2010, Tantanarat et al, 2012, Saier and Ballou, 1968, Xi et al, 2014). Thus, the conditions that promote IS 5 hopping into the glpFK -activating site could have evolved under the pressures of natural selection.…”