N-Sorbose

On the other hand, the product from glucose is an exceedingly complex mixture, the composition of which varies with the conditions of treatment. D-Psicose (from treatment with ammonia) (55) and (dl + n)-sorbose (from treatment with a strong base resin) 90) have been identified definitely in the mixture. D-Glucose is readily converted to D-fructose. From the latter has been isolated after treatment with potassium hydroxide (dl + D)-sor-... 

One of the n-2-ketohcxoses is called sorbose. On treatment with NaJBH4, sorbose yields a mixture of gulitol and iditol. What is the structure of sorbose ... 

When D-fructose and L-sorbose are refluxed with aqueous HC1, dihexulose dianhydrides are formed.91 If the water is replaced by N./V-dimethylformamide, substantially increased yields are obtained and 1,2-linked disaccharides are detected. Higher yields of dianhydrides were obtained from fructose, rather than sorbose, under comparable conditions. Treatment of levan with dilute H2S04 at 60°C yielded92 a-D-Fru/-l,2 2,1 -fi-D-Fru/(5). Presumably, any products that contain 2,6-linkages with large central rings would rapidly isomerize to the more stable 1,2-linked product. 

Figure 6. Side view of energetically most favorable complex formed between L-sorbose and hexamethylentetramine (HMTA) auxiliary. Complex is stabilized by N-H-O hydrogen bond interaction.

Important results have recently been obtained by Simon. Among other things he ascertained that glycerol yields butyric acid. The formation of four-carbon compounds from six-carbon substrates is independent of the grouping (aldehyde, hydroxyl, carboxyl, phosphory-lated hydroxyl) at the first carbon atom of the molecule. L-Rhamnose and D-arabitol are fermented, but not n-arabinose and D-sorbitol. In contrast to the studies of Underkofler and Hunter, " L-sorbose has been found fermentable. Results obtained with fresh and acetone-dried Cl. hutylicum are identical in principle. 

L-Iditol (sorbi6rite), the last of the four naturally occurring hexitols, occurs in service berries along with sorbitol. After removing sorbitol from the juice by fermentation to L-sorbose with the sorbose bacterium, Acetobacter xylinum, the n-iditol is crystallized as a benzylidene derivative. It has been prepared by the action of sodium amalgam on... 

L-Glucitol (n-gulitol), the enantiomorph of sorbitol, has been obtained by the action of sodium amalgam on D-gulonolactone or, along with D-iditol, on D-sorbose. ... 

Early contributions to the oxidation of n-alcanols at nickel hydroxide electrodes have been described elsewhere More recent work is summarized in Table 1. Newer applications of the electrode, especially to the oxidation of 2,3 4,6-di-O-isopropylidene-L-sorbose (/) to L-gulonic acid (2), a step in a commercial vitamin C synthesis, were started by Vertes The development of the latter conversion to an industrial scale process was achieved by Robertson and Seiler . The mechanism... 

Sorbosan Trinitrate. C6H705(N02)3 mw 297.13 N 14.14% OB to C02 -24.23% cryst mp 40—54°. Sol in ethanol. Prepn is by soln of sorbose in cold (0°) nitric acid followed by pouring the soln into well stirred sulfuric acid also at 0°. The prod is then pptd, filtered off,... 

A. Ishizu, K. Yoshida, and N. Yamazaki, L-Galactosaccharinic acids new saccharinic acids formed by calcium hydroxide treatment of L-sorbose, Carbohydr. Res., 23 (1972) 23-29. 

A N-glycoside of L-sorbose, p-phenetidine L-sorboside, was synthesized in low yield by Kuhn and Birkofer.122 L-Sorbose was condensed in... 

The Synthesis of Sugars from Simpler Substances. Part IV. Enzymic Synthesis of 6-Deoxy-u-fructose and 6-Deoxy-L-sorbose, L. Hough and J. K. N. Jones,/. Chem. Soc., (1952) 4052-4055. 

Preparation of L-Sorbose from 5-Keto-D-gluconic Acid (L-Sorburonic Acid), J. K. N. Jones and W. W. Reid, Can. /. Chem., 33 (1955) 1682-1683. 

In works made under direction of N.M. Emanuel they showed that catalytic system [Cu2+... A. .. 02] where A" - the anion form of substrate (anion form of substrate was formed at the expense of its deprotonation under the action of bases introduced into the system) is extremely effective in reactions of oxidation of fluorinated alcohols with general formula H(CF2CF2)nCH2OH (where n=l-6) [2], camphor [3] and diacetone-L-sorbose [4] with... 

For the carbohydrates especially, the amount of available crystal structural data decreases sharply with molecular complexity [479]. With the exception of the cyclodextrins, discussed in Part III, Chapter 18, there are less than 40 crystal structure analyses of oligosaccharides, of which less than 10 are trisaccharides, one is a tetrasaccharide, and one a hexasaccharide (Part III, Chap. 18). The majority of the basic monosaccharides that are the subunits of the polysaccharides that occur naturally have been studied for example, the pyranose forms of /7-arabinose, a-xylose, a- and -glucose, / fructose, a-sorbose, a-mannose, a- and -galactose, a-fucose, a-rhamnose, N-acetyl glucosamine, and mannosamine (Box 13.2). How-... 

The unusual utility of this adsorbent has been demonstrated by its role in the preliminary isolation of isomaltose,maltotriose, maltotetra-086, = and panose > from the hydrolytic products of starch in the preparation of n-xylo-biose, -trio.se, -tetraose, -pentaose, -hexaose, and -heptaose from a partially hydrolyzed xylan in the resolution of bi-molecular dianhydrides of L-sorbose < and D-fructose < > in an improved procedure for the preparation of stachyose and in the preparation of a series of maltodextrins (as high as maltoheptaose) from the partial, acid... 

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