Syntheses of enediyneribofuranosides
Item
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Title
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Syntheses of enediyneribofuranosides
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Identifier
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d_2009_2013:9bc47500d436:10794
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identifier
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11106
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Creator
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Therese, Soosairaj,
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Contributor
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Panayotis Meleties
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Date
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2011
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Language
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English
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Publisher
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City University of New York.
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Subject
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Organic chemistry | Chemistry | 2 | 3 | 5-O-tribenzyl-D-ribonolactone | Benzeneconjugated enediynes | enediyneribosides | enediynes | ethynylribosides | isopropylideneribonolactone
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Abstract
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Enediynes are natural bacterial products isolated in the 1980s. They are characterized by nine- or 10-memberd rings containing two triple bonds separated by a double bond. These molecules have powerful antitumor activity. The enediyne moiety, which is often referred as "war head", undergoes Bergman cyclization to form a highly reactive 1,4-benzenoid diradical. These radicals cleave the DNA strand by hydrogen abstraction. Calicheamicin, esperamicin, dynemicin, and neocarzinostatin are some natural enediynes which are biologically active against Gram-positive and Gram-negative bacteria, Leukemia P388, Murine tumors P388, B16, Melanoma B16, and Tumor cells including L1210.;Despite of their biological activity, the usefulness of natural enediynes as therapeutic agents have been limited due to their poor selectivity for the cancer cells. The structural complexity of the natural compounds also makes their synthesis cumbersome. So the quest for developing synthetic analogs by incorporating enediyne functional group on various substrates has been developed. Carbohydrate based enediynes have rarely been reported as templates for enediyne molecules. Careful study of the structures and biological activity of natural enediynes reveals that the carbohydrate part of these molecules plays a crucial role in the selectivity. So the goal of this research attempt is to design unique reaction schemes to synthesis a new class of enediynes on carbohydrate substrate such as ribose which are expected to have better selectivity for the target cell.
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Type
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dissertation
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Source
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2009_2013.csv
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degree
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Ph.D.
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Program
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Chemistry
