50-99-7

History

D(+)-Glucose?is the most important and predominant monosaccharide found in nature. It was isolated from raisins by Andreas Sigismund Marggraf (1709–1782) in 1747, and in 1838, Jean-Baptiste-André Dumas (1800–1884) adopted the name glucose from the Greek word glycos meaning sweet. Emil Fischer (1852–1919) determined the structure of glucose in the late 19th century. Glucose also goes by the names dextrose (from its ability to rotate polarized light to the right), grape sugar, and blood sugar. The term blood sugar indicates that glucose is the primary sugar dissolved in blood. Glucose’s abundant hydroxyl groups enable extensive hydrogen bonding, and so glucose is highly soluble in water.

Manufacturing Process

D-Glucose is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement.Dehydration of Dextrose Monohydrate.1. Dehydration with Fluid-bed DryerDextrose monohydrate was brought in a horizontal-placed turbo-dryer (VOMM, Mailand, Italy). The dehydration occurred at a temperature of between 90° to 150°C in a stream of air of 5 Normalised m3/kg (i.e volume of gas at 0°C and 1 mbar) dextrose and a rotation speed of 1200 min-1.Dehydration of Glucose Syrup (Dextrose Content 96%).A glucose syrup (C*SWEET D 02763 Cerestar) (dry substance ca. 70%) was sprayed at a flow rate of 7 kg/h at 70°C into a Niro FSD pilot plant spray dryer. For powdering ca. 9 kg coarsely milled dried product at a ratio liquid/solid of 1:2 was added. The atomising conditions were as follows:The drying chamber was operated at:The fluid bed was adjusted to:

Biotechnological Production

The D-configuration of D-isoascorbic acid at C5 allows a short biosynthetic pathway from D-glucose, i.e., its 1,5-glucopyranoside, which is oxidized to D-glucono-1,5-lactone by glucose oxidase followed by oxidation at C2 by D-gluconolactone oxidase. The immediate oxidation product of D-glucono-1,5-lactone by gluconolactone oxidase already has reducing activity on, e.g., 2,6-dichlorphenolindophenol. It is rather stable at pH 4. Upon pH shift, this compound spontaneously converts to D-isoascorbic acid. The unidentified immediate oxidation product could be 2-keto-D-glucono-1,5-lactone, which rearranges via a reversible transesterification reaction to the 1,4-lactone followed by an irreversible enolization to D-isoascorbic acid. The formation of 2-keto-D-gluconic acid as the result of 2-keto-D-glucono-1,5-lactone hydrolysis was not reported. The oxidation of the 1,4-lactone by D-gluconolactone oxidase might also occur to some extent, since D-glucono-1,5-lactone shows a tendency to slowly rearrange to the 1,4-lactone at pH[4and the D-gluconolactone oxidase of Penicillium cyaneofulvum accepts both D-glucono-1,5-lactone and the corresponding 1,4-lactone . This reaction would directly deliver the keto-isomer of D-isoascorbic acid. The sequence of the reactions from D-glucose to D-isoascorbic acid, first oxidation at C1, then oxidation at C2 (C1, C2), is similar to the naturally evolved Asc biosynthesis from L-galactose or L-gulose. Oxidation of D-gluconolactone at C2 is also afforded by pyranose-2-oxidase from Polyporus obtusus. In this reaction both D-isoascorbic acid and 2-keto- D-gluconic acid were obtained in a roughly 1:1 ratio. Obviously, following the natural C1, C2 oxidation sequence, transesterification and (iso)ascorbic acid formation are preferred over hydrolysis and 2-keto sugar acid formation or are at least possible to a significant extent. If the sequence of oxidation reactions is reversed (C2, C1), i.e., D-glucopyranose is first oxidized by pyranose-2-oxidase to D-glucosone followed by glucose oxidase treatment, 2-keto-D-gluconate was reported as the only oxidation product. Though not explicitly reported, it is safe to assume that the later oxidation occurs with 2-keto-D-gluco-1,5-pyranose and delivers as the immediate reaction product 2-keto-D-glucono-1,5-lactone, which hydrolyzes affording 2-keto-D-gluconate. It is unclear why the spontaneous follow-up reaction of 2-keto-D-glucono-1,5-lactone delivers, at least to some extent, D-isoascorbic acid if obtained according to the C1, C2 reaction sequence, but only 2-keto-D-gluconate if obtained by the C2, C1 oxidation sequence.

Air & Water Reactions

Water soluble.

Reactivity Profile

A weak reducing agent.

Health Hazard

No toxicity

Biochem/physiol Actions

Glycogen phosphorylase, muscle associated (PYGM), is an important contributor to glycogenolysis. Down regulation of PYGM gene is observed in schizophrenia. Mutation in PYGM leads to McArdle disease, a glycogen storage disorder. The PYGM gene is significantly associated with energy production.

Safety Profile

Mildly toxic by ingest ion. An experimental teratogen. Experi mental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Potentially explosive reaction with potassium nitrate + sodium peroxide when heated in a sealed container. Uxtures with alkali release carbon monoxide when heated. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise -D-glucose from hot glacial acetic acid or pyridine. Traces of solvent are removed by drying in a vacuum oven at 75o for >3hours. [Gottfried Adv Carbohydr Chem 5 127 1950, Kjaer & Lindberg Acta Chem Scand 1 3 1713 1959, Whistler & Miller Methods in Carbohydrate Chemistry I 1301962, Academic Press, Beilstein 1 IV 4306.] [For equilibrium forms see Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972.]

General Description

D(+)-Glucose can be selectively detected in aqueous solutions through a fluorescence turn-on mechanism involving its enzymatic oxidation by glucose oxidase (GOx) to produce hydrogen peroxide (H2O2), which then reacts with a modified tetraphenylethylene (TPE)-based probe. This reaction triggers aggregation-induced emission (AIE), resulting in a measurable fluorescence signal, demonstrating high sensitivity and specificity for D-glucose with a detection limit as low as 3.0 μM. The method is highly selective, showing minimal interference from other sugars or reactive oxygen species.

Definition

Naturally occurring GLUCOSE belongs to the stereochemical series D and is dextrorotatory, indicated by the symbol (+). Thus the term dextrose is used to indicate D-(+)-glucose. As other stereochemical forms of glucose have no significance in biological systems the term ‘glucose’ is often used interchangeably with dextrose in biology.