Ruff Degradation
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Ruff Degradation
Ruff degradation is a reaction used to shorten the open chain forms of monosaccharides. It is functionally the reverse reaction of Kiliani-Fischer synthesis. In 1898, Otto Ruff published his work on the transformation of D- Glucose to D-Arabinose later called the Ruff degradation. In this reaction, D-Glucose is converted to D-Arabinose. In this reaction, the terminal aldehyde group is converted to a carboxylic acid group, using selective oxidation of the aldehyde using Bromine water Bromine water is an oxidizing, intense brown mixture containing diatomic bromine (Br2) dissolved in water (H2O). It is often used as a reactive in chemical assays of recognition for substances which react with bromine in an aqueous environment wi ... and then converted to gluconate ion. Next, Fe(OAc)3 with 30% of H2O2 is added. Thus COO- ion will form and a stereo selective compound will form. And below -CH2OH will convert to -CHO group through the reduction of iron from its +3 state to +2 state, t ...
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Otto Ruff
Otto Ruff (12 December 1871 – 17 September 1939) was a German chemist. Life Otto Ruff was born in Schwäbisch Hall, Württemberg. After becoming a pharmacist under the supervision of Carl Magnus von Hell (known from the Hell-Volhard-Zelinsky halogenation) at the University of Stuttgart he joined the group of Hermann Emil Fischer at the University of Berlin. Fischer was noted for his work on carbohydrates (sugars) and so Ruff started his career as an organic chemist. In 1898 he published his work on the transformation of d-Glucose to d-Arabinose, later called the Ruff degradation. Supported by the far-sighted Fischer, who recognized that while organic chemistry was now mature, physical chemistry was growing rapidly, Ruff became head of the new inorganic department in Berlin, working alongside Alfred Stock who was five years his junior. This drastic change in subject benefited Ruff during his work on chlorides sulfur compounds. In 1902 he married Meta Richter, a pharmacist, an ...
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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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Arabinose
Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde.The D/L nomenclature does not refer to the molecule's optical rotation properties but to its structural analogy to glyceraldehyde. However, L-arabinose is in fact more common than D-arabinose in nature and is found in nature as a component of biopolymers such as hemicellulose and pectin. The L-arabinose operon, also known as the araBAD operon, has been the subject of much biomolecular research. The operon directs the catabolism of arabinose in ''E. coli'', and it is dynamically activated in the presence of arabinose and the absence of glucose. A classic method for the organic synthesis of arabinose from glucose is the Wohl degradation. : Etymology Arabinose gets its name from gum arabic, from which i ...
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Carboxylic Acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion. Examples and nomenclature Carboxylic acids are commonly identified by their trivial names. They at oftentimes have the suffix ''-ic acid''. IUPAC-recommended names also exist; in this system, carboxylic acids have an ''-oic acid'' suffix. For example, butyric acid (C3H7CO2H) is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid. Alternately, it can be named as a "carboxy" or "carboxylic acid" substituent on another ...
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Bromine
Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig (in 1825) and Antoine Jérôme Balard (in 1826), its name was derived from the Ancient Greek (bromos) meaning "stench", referring to its sharp and pungent smell. Elemental bromine is very reactive and thus does not occur as a native element in nature but it occurs in colourless soluble crystalline mineral halide salts, analogous to table salt. In fact, bromine and all the halogens are so reactive that they form bonds in pairs—never in single atoms. While it is rather rare in the Earth's crust, the high solubility of the bromide ion (Br) has caused its accumulation in the oceans. Commercial ...
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Emil Fischer
Hermann Emil Louis Fischer (; 9 October 1852 – 15 July 1919) was a German chemist and 1902 recipient of the Nobel Prize in Chemistry. He discovered the Fischer esterification. He also developed the Fischer projection, a symbolic way of drawing asymmetric carbon atoms. He also hypothesized lock and key mechanism of enzyme action. He never used his first given name, and was known throughout his life simply as Emil Fischer. Early years and career Fischer was born in Euskirchen, near Cologne, the son of Laurenz Fischer, a businessman, and his wife Julie Poensgen. After graduating he wished to study natural sciences, but his father compelled him to work in the family business until determining that his son was unsuitable. Fischer then attended the University of Bonn in 1871, but switched to the University of Strasbourg in 1872. He earned his doctorate in 1874 under Adolf von Baeyer with his study of phthaleins, and was appointed to a position at the university. After eight ye ...
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Glyceraldehyde
Glyceraldehyde (glyceral) is a triose monosaccharide with chemical formula C3 H6 O3. It is the simplest of all common aldoses. It is a sweet, colorless, crystalline solid that is an intermediate compound in carbohydrate metabolism. The word comes from combining glycerol and aldehyde, as glyceraldehyde is glycerol with one alcohol group oxidized to an aldehyde. Structure Glyceraldehyde has one chiral center and therefore exists as two different enantiomers with opposite optical rotation: * In the nomenclature, either from Latin ''Dexter'' meaning "right", or from Latin ''Laevo'' meaning "left" * In the R/S nomenclature, either R from Latin ''Rectus'' meaning "right", or S from Latin ''Sinister'' meaning "left" While the optical rotation of glyceraldehyde is (+) for ''R'' and (−) for ''S'', this is not true for all monosaccharides. The stereochemical configuration can only be determined from the chemical structure, whereas the optical rotation can only be determined em ...
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Name Reactions
A name reaction is a chemical reaction named after its discoverers or developers. Among the tens of thousands of organic reactions that are known, hundreds of such reactions are well-known enough to be named after people. Well-known examples include the Grignard reaction, the Sabatier reaction, the Wittig reaction, the Claisen condensation, the Friedel-Crafts acylation, and the Diels-Alder reaction. Books have been published devoted exclusively to name reactions;Alfred Hassner, C. Stumer. ''Organic syntheses based on name reactions''. Elsevier, 2002. Li, Jie Jack. ''Name Reactions: A Collection of Detailed Reaction Mechanisms''. Springer, 2003. the Merck Index, a chemical encyclopedia, also includes an appendix on name reactions. As organic chemistry developed during the 20th century, chemists started associating synthetically useful reactions with the names of the discoverers or developers; in many cases, the name is merely a mnemonic. Some cases of reactions that were not reall ...
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