Glucose isolation

Proof of Constitution.—The method of synthesis from methyl 6-trityl-ajS-D-glucofuranoside furnished strong evidence that the trimethyl-D-glucose isolated by Smith121 was substituted at positions 2, 3 and 5. This conclusion was confirmed by the observations (a) that the trimethyl-gluconolactone, produced when the sugar was oxidized with bromine... 

Proof of Constitution.—Since the crystalline a- and 8-forms of 3,4,6-trimethyl-D-glucose, isolated by Sundberg and coworkers,28 were each obtained by hydrolysis of methyl 3,4,6-trimethyl-/3-D-glucopyrano-side,82,154 the proof of the constitution of this glucoside obviously played an important part in the characterization of the trimethylglucose itself. Unfortunately, there is no such crystalline reference compound to correlate the earliest samples of sirupy 3,4,6-trimethyl-D-glucose157,168 with the crystalline specimens isolated by Sundberg and coworkers. 

In the six-carbon series,8 the selective hydrogenation of d-ardbo-tetraacetoxy-l-nitrohexene-1 gave crystalline l-nitro-l,2-didesoxy-D-aro o-hexitol tetraacetate in 79 percent yield. This product, on de-acety-lation followed by the Nef reaction, then gave D-ara6o-2-desoxyhexose ( 2-desoxy-D-glucose ), isolated as the benzylphenylhydrazone,60 in high yield. 

It should be possible to improve the efficiency of the cellulose enzyme complex for hydrolyzing cellulose to glucose. The enzyme complex apparently contains decrystallizing and hydrolysis enzymes that work together to convert cellulose to glucose. Isolation of the specific enzymes and genetic engineering could provide a more efficient complex. 

Some unusual aminosaccharides can have antibacterial and antibiotic effects this is the case of 3-amino-3-deoxy-D-glucose isolated from deep-sea bacteria (a Bacillus strain) collected at a depth of 4310 m [178]. More importantly, cellular receptors responsible for the adherence of microbes to eukaryotic cells are often lectin-type adhesins [179], and aminosaccharide treatment can result in the protection against microbial infections [ 180]. 

Wolfrom and Shilling have observed that water is an extremely poor catalyst for these reactions. Thus, it was necessary to heat an 80% solution of D-fructose at 113° for 16 hours in order to produce a 0.1% yield of n-glucose (isolated as 1,2,3,4,6-penta-O-acetyl-D-glucose). This conversion may have been aided by a slight oxonium-ion catalysis, since, although the initial pH of the reaction mixture was 6.9, the final pH was 2.7. 

C -labeled sugars have been prepared both by biosynthetic and synthetic methods (Chapter II). P. j beled sugar phosphates have also been produced biosynthetically (22). Biosynthetically produced C -labeled sugars are of limited value because of the distribution of label between the various carbon atoms. The 3,4-C Mabeled glucose isolated from liver glycogen (41) is an exception. 

Solasodine trioside Solasodine 2 D-Xylose, D-glucose IsoL 75, 197... 

Soladulcamarine Tomatidenol 2 L-Rhamnose, L-arabinose, D-glucose Isol. 25, 116... 

Solanidine trioside Solanidine Rhamnose, abinose, glucose Isol. 160... 

D-Glucose reacted with diaminomaleonitrile in acetic acid to yield the A -(2-amino-l, 2-dicyanoethenyl)-)8-D-glucopyranosylamine derivative (149). jS-D-GIucopyranosylamine and 2 amino-2-deoxy-D-glucose (isolated as the fully acetylated derivatives) were produced in low yield on u.v.-irradiation of aqueous solutions of D-glucose and glycine or L-lysine. ... 

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