Monosaccharide Sugars: Chemical Synthesis by Chain Elongation, Degradation, and Epimerization

Elsevier
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In a single volume, Monosaccharide Sugars critically summarizes the applied and potentially useful strategies for the synthesis and degradation of monosaccharides by chain-elongation, degradation, and epimerization. These methodologies permit the synthesis of rare or unnatural monosaccharides that are frequently employed as chiral building blocks in natural products synthesis, as well as for producing sugar derivatives labeled with radioactive isotopes. Representative and well-established experimental procedures are provided to illustrate the potential of the synthetic transformation.Degradation of carbohydrates also represents an invaluable tool for the structural elucidation of certain natural products, suchas glycosides, antibiotics, and polysaccharides. When describing the individual methods, unique supplementary collections of the prepared sugar derivatives are shown in tabular form. This compendium will eliminate tedious literature searches for those engaged in research and teaching on the chemistry and biochemistry of saccharides and other natural products, and also for those working on the medicinal and metabolic investigation of related substances of biological importance.
  • Illustrates the practical potential of well-established experimental procedures in synthetic transformations
  • Provides supplementary collections of prepared sugar derivatives in tabular form
  • Summarizes in a single volume the methods of obtaining carbohydrate-derived compounds
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Additional Information

Publisher
Elsevier
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Published on
Jan 22, 1998
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Pages
508
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ISBN
9780080536989
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Language
English
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Genres
Science / Chemistry / Organic
Science / Life Sciences / Biochemistry
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Content Protection
This content is DRM protected.
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Eligible for Family Library

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Inhaltsangabe:Introduction: Metabolic reduction is the counterpart to oxidative pathways and plays an important role in the phase-I metabolism of carbonyl group bearing substances. Carbonyl reduction means the formation of a hydroxy group from a reactive aldehyde or ketone moiety and is generally regarded as an inactivation or detoxification step since the resulting alcohol is easier to conjugate and to eliminate. Not only are these carbonyl-containing compounds widespread in the environment and enter the body as xenobiotics and environmental pollutants, but they can also be generated endogenously through normal catabolic oxidation and deamination reactions. Many endogenous compounds such as biogenic amines, steroids, prostaglandins and other hormones are metabolized through carbonyl intermediates. In addition, lipid peroxidation within the cell results in the production of reactive carbonyls such as acrolein, 4-hydroxynonenal, 4-oxononenal and malon-dialdehyde, while oxidative damage to DNA generates base propenals. Dietary sources of carbonyl-containing compounds are diverse and include aldehydes found in fruits as well as the breakdown product of ethanol, acetaldehyde. Pharmacologic drugs represent further sources of exposure to carbonyl-containing compounds. From the pharmacologist s point of view, carbonyl reduction has been shown to be of significance in various inactivation processes of drugs bearing a carbonyl group. On the other hand, the carbinols formed may retain therapeutic potency, thus prolonging the pharmacodynamic effect of the parent drug, or, in some instances, a compound gains activity through carbonyl reduction. From the toxicologist s point of view, carbonyl reduction plays an important role in the toxification of drugs such as daunorubicin and doxorubicin (cf. chapter 4), whereas numerous reports corroborate the concept of carbonyl-reducing enzymes being involved in detoxification processes of endogenous and xenobiotic reactive carbonyl compounds. Compared with the oxidative cytochrome P450 (CYP) system, carbonyl-reducing enzymes had, for a long time, received considerably less attention. However, the advancement of carbonyl reductase molecular biology has allowed the identification and characterization of several carbonyl-reducing enzymes, including pluripotent hydroxysteroid dehydrogenases that are involved in xenobiotic carbonyl compound metabolism, in addition to catalyzing the oxidoreduction of their physiologic [...]
Master's Thesis from the year 2014 in the subject Chemistry - Bio-chemistry, grade: A, , course: Biotechnology, language: English, abstract: Peach is the most commonly eaten stone fruit which grows in the temperate regions of the world. These are also among the most exported fruits in term of volume and value. Peaches, being perishable and susceptible to microbial spoilage, have a short shelflife. The goal of this study was to determine the effect of gamma irradiation on the microbiological and organoleptic properties of peaches and secondly, to determine the effects of irradiation on shelf-life of the fruit. The fruit (local variety, No.4), at proper maturity stage was collected and irradiated with 0.25, 0.5, and 0.75kGy dose, stored under refrigerated (4 o C) conditions for a period of three weeks. Total viable count, Gram negative Enterobacteriaceae count, Salmonella-Shigella count, yeast and mold count, loss in weight and decay percentage was evaluated after 7, 14 and 21 days of storage (4 o C). Data obtained from microbiological and sensory evaluations of irradiated peaches was compared with the observations obtained from unirradiated (control) samples. Microbial evaluation of the fruits revealed the presence of Salmonella sonnie on SS agar and non fermentor spp. on macConkey agar. Ten types of yeasts were isolated on potato dextrose agar and analyzed microscopically. Studies showed total bacterial, yeast and molds significantly decreased with increasing dose level. The sensory evaluation of the fruits revealed that irradiation preserves the texture and appearance of fruit. The gamma-irradiation dose of 0.75kGy proved to be effective in reducing weight loss and significantly (p≤0.05) delaying the decaying of the fruit by 7 days under refrigerated (4 o C) conditions. Statistical studies were carried out using Duncan’s multiple range test (DMRT) and means were separated by LSD at 5 %. It is hoped that this particular type of research will help in improving export quality of peaches.
Internship Report from the year 2015 in the subject Chemistry - Bio-chemistry, grade: 1.0, University of Constance, language: English, abstract: One interesting aspect is the involvement and the relevance of one sole enzyme in the microbial tauropine degradation pathway: the tauropine dehydrogenase. Therefore three main questions were studied. The first was to verify the action of a tauropine dehydrogenase in microorganisms. The second step was to further characterize this enzyme by its molecular weight and its localization within bacterial cells. In addition, the degradation pathway downstream of the potential tauropine dehydrogenase should be clarified. Therefore, in this study, the metabolism of tauropine in four different model organisms was investigated. As model organisms a Ralstonia strain from fresh water was used and in addition three terrestrial bacterial strains were isolated. The metabolism of tauropine in microorganisms is not yet clarified. Tauropine, besides other opines, has also been reported in the context of bacteria. In fact, it was found in plants, which were infected by agrobacteria with a virulent Ti plasmid. The resulting genetic modification leads to tumor formation, and the plant is triggered to produce opines. As plants cannot use opines themselves, the opines serve as nutrition for the agrobacteria and other opine-degrading bacterial strains. But so far, compared to marine animal phyla, the intermediate steps in the degradation of tauropine in microorganisms are widely unknown. Preliminary investigation in marine bacteria like Ruegeria pomeroyi DSS-3 and Roseovarius nubinhibens ISM has shown that they can use tauropine as source of carbon and nitrogen. Sulfate thereby occurs as end product. It is possible, that the tauropine degradation in bacteria is analogous to that in invertebrates. This would mean that a dehydrogenase is involved. If in microorganisms tauropine can be degraded into pyruvate and taurine by a tauropine dehydrogenase, it is also possible that taurine is further metabolized in the processes, which are already quite well understood. Those processes could include the taurine dehydrogenase and desulfonation by sulfoacetaldehyde acetyltransferase.
Intrigued as much by its complex nature as by its outsider status in traditional organic chemistry, the editors of The Organic Chemistry of Sugars compile a groundbreaking resource in carbohydrate chemistry that illustrates the ease at which sugars can be manipulated in a variety of organic reactions.

Each chapter contains numerous examples demonstrating the methods and strategies that apply mainstream organic chemistry to the chemical modification of sugars. The book first describes the discovery, development, and impact of carbohydrates, followed by a discussion of protecting group strategies, glycosylation techniques, and oligosaccharide syntheses. Several chapters focus on reactions that convert sugars and carbohydrates to non-carbohydrate molecules including the substitution of sugar hydroxyl groups to new groups of synthetic or biological interest, cyclitols and carbasugars, as well as endocyclic heteroatom substitutions. Subsequent chapters demonstrate the use of sugars in chiral catalysis, their roles as convenient starting materials for complex syntheses involving multiple stereogenic centers, and syntheses for monosaccharides. The final chapters focus on new and emerging technologies, including approaches to combinatorial carbohydrate chemistry, the biological importance and chemical synthesis of glycopeptides, and the medicinally significant concept of glycomimetics.

Presenting the organic chemistry of sugars as a solution to many complex synthetic challenges, The Organic Chemistry of Sugars provides a comprehensive treatment of the manipulation of sugars and their importance in mainstream organic chemistry.

Daniel E. Levy, editor of the Drug Discovery Series, is the founder of DEL BioPharma, a consulting service for drug discovery programs. He also maintains a blog that explores organic chemistry.

“The bard of biological weapons captures the drama of the front lines.”—Richard Danzig, former secretary of the navy

The first major bioterror event in the United States-the anthrax attacks in October 2001-was a clarion call for scientists who work with “hot” agents to find ways of protecting civilian populations against biological weapons. In The Demon in the Freezer, his first nonfiction book since The Hot Zone, a #1 New York Times bestseller, Richard Preston takes us into the heart of Usamriid, the United States Army Medical Research Institute of Infectious Diseases at Fort Detrick, Maryland, once the headquarters of the U.S. biological weapons program and now the epicenter of national biodefense.

Peter Jahrling, the top scientist at Usamriid, a wry virologist who cut his teeth on Ebola, one of the world’s most lethal emerging viruses, has ORCON security clearance that gives him access to top secret information on bioweapons. His most urgent priority is to develop a drug that will take on smallpox-and win. Eradicated from the planet in 1979 in one of the great triumphs of modern science, the smallpox virus now resides, officially, in only two high-security freezers-at the Centers for Disease Control in Atlanta and in Siberia, at a Russian virology institute called Vector. But the demon in the freezer has been set loose. It is almost certain that illegal stocks are in the possession of hostile states, including Iraq and North Korea. Jahrling is haunted by the thought that biologists in secret labs are using genetic engineering to create a new superpox virus, a smallpox resistant to all vaccines.

Usamriid went into a state of Delta Alert on September 11 and activated its emergency response teams when the first anthrax letters were opened in New York and Washington, D.C. Preston reports, in unprecedented detail, on the government’ s response to the attacks and takes us into the ongoing FBI investigation. His story is based on interviews with top-level FBI agents and with Dr. Steven Hatfill.

Jahrling is leading a team of scientists doing controversial experiments with live smallpox virus at CDC. Preston takes us into the lab where Jahrling is reawakening smallpox and explains, with cool and devastating precision, what may be at stake if his last bold experiment fails.
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