Manno

Cyclic sulfates rapidly react with the fluoride ion sources to give monofluoro derivatives Thus, the 2,3-cyclic sulfate of methyl-4 6 O benzylidene p D manno pyranoside cleanly reacts with tetramethylammonium fluoride to give methyl 4,6-0-benzylidene 2 deoxy 2 fluoro-p-D-glucopyranoside-3-sulfate Acid hydrolysis followed by acetylation gives 2 deoxy 2 fluoro-P-D-glucopyranoside triacetate in 84% isolated yield [5S] (equation 38)... 

Manno-heptit, n. mannoheptitol. -zucker-saure, /. mannosaccharic acid. 

Treatment of methyl 2-azido-4,6-0-benzylidene-2-deoxy-a-D-altro-pyranoside (128) (42) with 121 followed by refluxing and processing afforded a chloro derivative as a sirup in 70% yield (46, 49). Reduction of this product with an excess of Raney-nickel in methanol containing acetic anhydride afforded a crystalline product, m.p. 179°C., which is formulated as the d-manno analog 131. The actual product is most likely methyl azido-4,6-0-benzylidene-3-chloro-2,3-dideodxy - a - d - mannopyran-oside (130) resulting from attack of chloride ion at C-3 with inversion of configuration in the intermediate 129. Had the chlorination proceeded... 

Manno CS, Pierce GF, Arrada VR et al (2006) Successful transduction of liver in hemophilia by AAV-Factor IX and limitations imposed by the host immune response. Nat Med 12(3) 342-347... 

N 14.97% OB to C02 -21,4% fine, asbestoslike needies mp 36°. Was prepd by Will and Lenze (Ref 2) by dissolving Oi-methyl-d-manno-site in cold coned nitric acid and adding coricd sulfuric acid dropwise with stirring. It is an expl which is relatively stable at 50° (weight loss 1.3% in 10 days, 7% in 12 days)... 

D-a/to D-altro D-gluco D-manno o-gulo D-ido D-galacto D-talo... 

D-ribo-Pentose for D-ribose D-manno-Hexose for D-mannose. 

D-glycero-D-galacto-HepMo not L-p/ycero-D-manno-heptitol... 

Amino-2-deoxymannose manno- Hexose ribo- Hex-2-ulose... 

Sulfinylacrylate 41 has been successfully used in the enantioselective synthesis of pseudo-sugar [46, 47]. Cycloaddition of (S)-3-(2-pyridylsulfinylacrylate) (41) with furan and 3,4-dibenzyloxyfuran under Et2AlCl catalysis afforded cycloadducts 42, 43 and 44 (Equation 3.12) which were converted into pseudo-manno-pyranoses 45, 46 and 47 (Figure 3.5). 

These results have been used to prepare key starting compounds 11 and 12 for the enantioselective synthesis of 3-deoxy-D-manno-2-octulosonic acid... 

Pyruvate-dependent lyases serve catabolic functions in vivo in the degradation of sialic acids and KDO (2-keto-3-deoxy-manno-octosonate), and in that of 2-keto-3-deoxy aldonic acid intermediates from hexose or pentose catabolism. 

Extensive studies have indicated that only pyruvate is acceptable as the NeuA donor substrate, with the exception of fluoropyruvate [49], but that the enzyme displays a fairly broad tolerance for stereochemically related aldehyde substrates as acceptor alternatives, such as a number of sugars and their derivatives larger or equal to pentoses [36,48,50,51]. Permissible variations include replacement of the natural D-manno configured substrate (4) with derivatives containing modifications such as epimerization, substitution, or deletion at positions C-2, -4, or -6 [16,27]. Epimeriza-tion at C-2, however, is restricted to small polar substituents owing to strongly... 

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