Hexosamines
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Hexosamines
Hexosamines are amino sugars created by adding an amine group to a hexose. Examples include: * Fructosamine (based upon fructose) * Galactosamine (based upon galactose) * Glucosamine (based upon glucose) * Mannosamine (based upon mannose Mannose is a sugar monomer of the aldohexose series of carbohydrates. It is a C-2 epimer of glucose. Mannose is important in human metabolism, especially in the glycosylation of certain proteins. Several congenital disorders of glycosylation ...) External links * * {{organic-compound-stub ...
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Glucosamine
Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country. Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug. Dietary supplement Oral glucosamine is a dietary supplement and is not a prescription drug. Glucosamine is marketed as a supplement to support the structure and function of joints, and the marketing is targeted to people with osteoarthritis. Commonly sold forms of glucosamine are glucosamine sulfate, glucosamine chondroitin, glucosamine hydrochloride, and ''N''-acetylglucos ...
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Fructosamine
Fructosamines are compounds that result from glycation reactions between a sugar (such as fructose or glucose) and a primary amine, followed by isomerization via the Amadori rearrangement. Biologically, fructosamines are recognized by fructosamine-3-kinase, which may trigger the degradation of advanced glycation end-products (though the true clinical significance of this pathway is unclear). Fructosamine can also refer to the specific compound 1-amino-1-deoxy-D-fructose ( isoglucosamine), first synthesized by Nobel laureate Hermann Emil Fischer in 1886. Most commonly, fructosamine refers to a laboratory test for diabetes management that is rarely used in human clinical practice (simple blood glucose monitoring or hemoglobin A1c testing are preferred). In small animal veterinary practice however it is part of the diabetic cat or dog diagnosis and monitoring giving an indication of blood glucose levels over the previous week. Many direct-to-consumer lab testing companies sell fruct ...
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Galactosamine
Galactosamine is a hexosamine derived from galactose with the molecular formula C6H13NO5. This amino sugar is a constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH). Precursors such as uridine diphosphate (UDP), UDP-''N''-acetyl-D-glucosamine, or glucosamine are used to synthesize galactosamine in the human body. A derivative of this compound is ''N''-acetyl-D-galactosamine. Galactosamine is a hepatotoxic, or liver-damaging, agent that is sometimes used in animal models of liver failure. Hepatotoxicity Galactosamine is used to induce hepatitis in rodent liver for research purposes. The result of using galactosamine to induce hepatitis is a disease model in which there is necrosis and inflammation of the liver. This type of tissue damage triggered by galactosamine resembles drug-induced liver disease in humans. Mechanism of hepatotoxicity The proposed mechanism behind galactosamine-induced hepatitis is depletion ...
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Mannosamine
D-Mannosamine (2-amino-2-deoxymannose) is a hexosamine derivative of mannose. See also * Neuraminic acid Neuraminic acid (5-amino-3,5-dideoxy-D-''glycero''-D-''galacto''-non-2-ulosonic acid) is an acidic (in particular ulosonic) amino sugar with a backbone formed by nine carbon atoms. Although 9-carbon sugars do not occur naturally, neuramini ... References Hexosamines {{Organic-compound-stub ...
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Alpha-D-Glucose
Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is -glucose, while -glucose is produced synthetically in comparatively small amounts and is less biologically active. Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. ...
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Amino Sugar
In organic chemistry, an amino sugar (or more technically a 2-amino-2-deoxysugar) is a sugar molecule in which a hydroxyl group has been replaced with an amine group. More than 60 amino sugars are known, with one of the most abundant being ''N''-Acetyl--glucosamine, which is the main component of chitin. Derivatives of amine containing sugars, such as ''N''-acetylglucosamine and sialic acid, whose nitrogens are part of more complex functional groups rather than formally being amines, are also considered amino sugars. Aminoglycosides are a class of antimicrobial compounds that inhibit bacterial protein synthesis. These compounds are conjugates of amino sugars and aminocyclitols. Synthesis From glycals Glycals are cyclic enol ether derivatives of monosaccharides, having a double bond between carbon atoms 1 and 2 of the ring. ''N''-functionalized of glycals at the C2 position, combined with glycosidic bond formation at C1 is a common strategy for the synthesis of amino sugars. T ...
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Amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. A ...
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Hexose
In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol. Hexoses exist in two forms, open-chain or cyclic, that easily convert into each other in aqueous solutions. The open-chain form of a hexose, which usually is favored in solutions, has the general structure H–(CHOH)''n''−1–C(=O)–(CHOH)4−''n''–H, where ''n'' is 1, 2, or 3. Namely, five of the carbons have one hydroxyl functional group (–OH) each, connected by a single bond, and one has an oxo group (=O), forming a carbonyl group (C=O). The remaining bonds of the carbon atoms are satisfied by seven hydrogen atoms. The carbons are commonly numbered 1 to 6 starting at the end closest to the carbonyl. Hexoses are extremely important in biochemistry, both as isolated molecules (such as glucose and fructose) and as building blocks of other compounds such as starch, cellulose, and glycosides. Hexose ...
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Fructose
Fructose, or fruit sugar, is a Ketose, ketonic monosaccharide, simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood. Fructose was discovered by French chemist Augustin-Pierre Dubrunfaut in 1847. The name "fructose" was coined in 1857 by the English chemist William Allen Miller. Pure, dry fructose is a sweet, white, odorless, crystalline solid, and is the most water-soluble of all the sugars. Fructose is found in honey, tree and vine fruits, flowers, Berry, berries, and most List of root vegetables, root vegetables. Commercially, fructose is derived from sugar cane, sugar beets, and maize. Hi ...
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Galactose
Galactose (, '' galacto-'' + '' -ose'', "milk sugar"), sometimes abbreviated Gal, is a monosaccharide sugar that is about as sweet as glucose, and about 65% as sweet as sucrose. It is an aldohexose and a C-4 epimer of glucose. A galactose molecule linked with a glucose molecule forms a lactose molecule. Galactan is a polymeric form of galactose found in hemicellulose, and forming the core of the galactans, a class of natural polymeric carbohydrates. D-Galactose is also known as brain sugar since it is a component of glycoproteins (oligosaccharide-protein compounds) found in Nerve tissue, nerve tissue. Etymology The word ''galactose'' was coined by Charles Weissman in the mid-19th century and is derived from Greek ''galaktos'' (of milk) and the generic chemical suffix for sugars ''-ose''. The etymology is comparable to that of the word '' lactose'' in that both contain roots meaning "milk sugar". Lactose is a disaccharide of galactose plus glucose. Structure and isomerism Gal ...
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Glucose
Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is -glucose, while -glucose is produced synthetically in comparatively small amounts and is less biologically active. Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Gluco ...
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