Mannose 2-deoxy-, 2-fluoro

Deoxy-3-fluoro-D-glucose (25%) and -mannose (40%) were prepared from 2-deoxy-2-fluoro-D-arabinose by a chain-extension reaction (cyanohydrin synthesis). Likewise, 4-deoxy-4-fluoro-D-glucose ° (27%) and -mannose (45%) were prepared from 3-deoxy-3-fluoro-D-arabinose. ... 

Coe and Bessell and coworkers studied the metabolic fates of 2-deoxy-2-fluoro-D-glucose (2DFG) and related compounds by using yeast hexokinase (as a model for mammalian hexokinase), and determined the kinetic constants K and V ) of the Michaelis-Menten equation D-glucose 0.17 (K in mAf)> 1 00 (relative value, D-glucose taken as 1) 2DG 0.59 0.11, 0.85 2DFG 0.19 0.03, 0.50 2-deoxy-2-fluoro-D-mannose (2DFM) 0.41 0.05, 0.85 2-deoxy-2,2-difluoro-D-nraZ>//Jo-hexose... 

Deoxy-2-[ F]fluoro-D-mannose ( F-2DFM) was prepared through treatment of 201 (see Section 11,2) with F-Bu4NF(MeCN, 75°, 30 min) or K F crown ether, as reported for the cold synthesis. F-2DFM was also prepared from methyl 4,6-di-0-acetyl-3-C>-benzoyl-2-C>-triflyl-a-D-glu-copyranoside with amino(polyether)-supported, carrier-free [ F]fluoride. 

The incorporation and metabolism of 2-deoxy-2-fluoro-D-[ H]glucose and -D-[ H]mannose in yeast and chick-embryo cells has been studied. 2-Deoxy-2-fluoro-D-glucose, 2-deoxy-2-fluoro-D-mannose, and their GDP and UDP derivatives were found to interfere with protein (involving that of... 

As 2-amino-2-deoxy-D-mannose is tumorstatic and 2-acetamido-2-deoxy-D-mannose 6-phosphate is an obligatory intermediate in the biosynthetic pathway to sialic acid, displacement of the essential OH-6 with a fluorine atom should be interesting from the biological viewpoint. 2-Acetamido-1,3,4-tri-0-acetyl-2,6-dideoxy-6-fluoro-D-mannopyranose (see Table 111 in Section 11,3) and its O- and A,0-deacetyl derivatives were prepared the first compound showed weak anticancer activity. 

T. Ido, C.N. Wan, V. Casella, J.S. Fowler, A.P. Wolf, M. Reivich, D.E. Kuhl, Labeled 2-deoxy-D-glucose analogs—F-18-labeled 2-deoxy-2-fluoro- o-glucose, 2-deoxy-2-fluoro- D-mannose and C-14-2-deoxy-2-fluoro- o-glucose, J. Label. Compds Radiopharm. 14 (1978) 175-183. 

At concentrations of amphomycin that completely block the formation of Man-P-Dol, the incorporation ofa-linked D-mannose into lipid-linked oligosaccharides is not completely inhibited.347 As was mentioned in Sections II,2,a and II,2,b, EDTA in vitro and 2-deoxy-2-fluoro-D-glucose in vivo have a similar effect, namely, the formation of a heptasaceharide-lipid, Man5(GlcNAc)2-PP-Dol, is still possible in the absence of Man-P-Dol. The question as to whether these D-man-nosyl residues come directly from GDP-Man is discussed in Section II,2,b. 

Stereoselective formation of the glycosidic bond can be achieved by this procedure. The dibutylstannylene complex of 3,4,6-tri-O-benzyl-D-mannose was converted into benzyl 3,4,6-tri-0-benzyl-f3-D-mannopyranoside, useful intermediate for the synthesis of 2-deoxy-2-[18F]fluoro-D-glucose [138]. 

M. Cerny, J. Dolezalova, J. Macova, J. Pacak, T. Trnka, and M. Budesinsky, Preparation of 3-deoxy-3-fluoro-D-mannose and its corresponding hexitol, Collect. Czech. Chem. Commun., 48 (1983) 2696-2700. 

Deoxy-2-fluoro-/3-mannose [XFMANP] a-Galactose [ADGALA01]... 

R, = OH, Rj = H, R2 = OH, R4 = CHjOH in Table 3), the enantiomeric compound of the one just reported could be easily prepared. Aldol condensation products were obtained as diastereomeric mixtures from L-sugars, such as L-fucose, L-xylose, L-lyxose, and o-sugars epimeric to o-mannose relative to the 3-position, such as D-allose and o-gulose [46-48]. Table 4 lists the corresponding aldol condensation products isolated as diastereomeric mixtures. Also, 3-deoxy-D-mannose by condensation with pyruvate gave a diastereomeric mixture of 6-deoxy-KDN furanose derivatives [43]. All these results confirm that sialic acid aldolase, similar to other aldolases, exhibits broad specificity toward the electrophilic acceptor on the other hand, only pyruvate was reported acceptable as the donor [10]. But very recently, in contradiction to that, 3-fluoro-Neu5Ac and 3-fluoro-KDN could be prepared by the sialic acid aldolase-catalyzed condensation of 3-fluoropyruvate and Af-acetylmannosamine or o-mannose (Scheme 5) [47]. 

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