Daunosamine
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Daunosamine
Daunosamine is a deoxy sugar and amino sugar of the Hexosamines, hexosamine class. Daunosamine is a component of the anthracycline class of antineoplastics, linked to a derivative of naphthacene. It is a component of birch juice. The compound is soluble in water and responds with polymers like cellulose and lignin if it is in excess, so collection of birch juice is very helpful for the birch tree. The dnrQ gene is required for the synthesis of daunosamine. Image:Daunorubicin2DACS.svg, Daunorubicin Image:Idarubicin.svg, Idarubicin Image:Doxorubicin Structure.png, Doxorubicin References External links

* {{MeshName, Daunosamine Hexosamines Deoxy sugars ...
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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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Pyranose
Pyranose is a collective term for saccharides that have a chemical structure that includes a six-membered ring consisting of five carbon atoms and one oxygen atom. There may be other carbons external to the ring. The name derives from its similarity to the oxygen heterocycle pyran, but the pyranose ring does not have double bonds. A pyranose in which the anomeric OH at C(l) has been converted into an OR group is called a pyranoside. Formation The pyranose ring is formed by the reaction of the hydroxyl group on carbon 5 (C-5) of a sugar with the aldehyde at carbon 1. This forms an intramolecular hemiacetal. If reaction is between the C-4 hydroxyl and the aldehyde, a furanose is formed instead. The pyranose form is thermodynamically more stable than the furanose form, which can be seen by the distribution of these two cyclic forms in solution. History Hermann Emil Fischer won the Nobel Prize in Chemistry (1902) for his work in determining the structure of the D-aldohexoses. How ...
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Deoxy Sugar
Deoxy sugars are sugars that have had a hydroxyl group replaced with a hydrogen atom. Examples include: * Deoxyribose, or 2-deoxy-D-ribose, a constituent of DNA * Fucose, or 6-deoxy-L-galactose, main component of fucoidan of brown algae, and present in N-linked glycans * Fuculose, or 6-deoxy-L-tagatose, one of the important components of avian influenza virus particles * Rhamnose, or 6-deoxy-L-mannose, present in plant glycosides In ''Escherichia coli'' bacteria, deoxyribose sugars are synthesized via two different pathways - one pathway involves aldol condensation, whereas the other pathway is conversion of a ribose sugar into a deoxyribose sugar by means of changes on the nucleotide or nucleoside level. Deoxyribose is synthesized through the reduction of ribose. Deoxyribose is derived from the same precursor as ribose being that the reduction of the sugar with the extra hydroxyl group results in the deoxy-sugar, which has its hydroxyl group replaced with a hydrogen atom. D ...
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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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Anthracycline
Anthracyclines are a class of drugs used in cancer chemotherapy that are extracted from ''Streptomyces'' bacterium. These compounds are used to treat many cancers, including leukemias, lymphomas, breast, stomach, uterine, ovarian, bladder cancer, and lung cancers. The first anthracycline discovered was daunorubicin (trade name Daunomycin), which is produced naturally by ''Streptomyces peucetius'', a species of Actinomycetota. Clinically the most important anthracyclines are doxorubicin, daunorubicin, epirubicin and idarubicin. The anthracyclines are among the most effective anticancer treatments ever developed and are effective against more types of cancer than any other class of chemotherapeutic agents. Their main adverse effect is cardiotoxicity, which considerably limits their usefulness. Use of anthracyclines has also been shown to be significantly associated with cycle 1 severe or febrile neutropenia. Other adverse effects include vomiting. The drugs act mainly by interc ...
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Naphthacene
Tetracene, also called naphthacene, is a polycyclic aromatic hydrocarbon. It has the appearance of a pale orange powder. Tetracene is the four-ringed member of the series of acenes. Tetracene is a molecular organic semiconductor, used in organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). In May 2007, researchers from two Japanese universities, Tohoku University in Sendai and Osaka University, reported an ambipolar light-emitting transistor made of a single tetracene crystal. Ambipolar means that the electric charge is transported by both positively charged holes and negatively charged electrons. Tetracene can be also used as a gain medium in dye lasers as a sensitiser in chemoluminescence. Jan Hendrik Schön during his time at Bell Labs (1997–2002) claimed to have developed an electrically pumped laser based on tetracene. However, his results could not be reproduced, and this is considered to be a scientific fraud. Napthacene is the main b ...
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Daunorubicin
Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. It is administered by injection into a vein. A liposomal formulation known as liposomal daunorubicin also exists. Common side effects include hair loss, vomiting, bone marrow suppression, and inflammation of the inside of the mouth. Other severe side effects include heart disease and tissue death at the site of injection. Use in pregnancy may harm the fetus. Daunorubicin is in the anthracycline family of medication. It works in part by blocking the function of topoisomerase II. Daunorubicin was approved for medical use in the United States in 1979. It is on the World Health Organization's List of Essential Medicines. It was originally isolated from bacteria of the ''Streptomyces'' type. Medical uses It slows or stops the growth of canc ...
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Idarubicin
Idarubicin or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts itself into DNA and prevents DNA unwinding by interfering with the enzyme topoisomerase II. It is an analog of daunorubicin, but the absence of a methoxy group increases its fat solubility and cellular uptake. Similar to other anthracyclines, it also induces histone eviction from chromatin. It belongs to the family of drugs called antitumor antibiotics. It is currently combined with cytosine arabinoside as a first line treatment of acute myeloid leukemia. It is used for treatment of acute lymphoblastic leukemia and chronic myelogenous leukemia in blast crisis. It is distributed under the trade names Zavedos (UK) and Idamycin (USA). Side effects Diarrhea, stomach cramps, nausea and vomiting Vomiting (also known as emesis and throwing up) is the involuntary, forceful expulsion of the contents of one's stomach through the mouth and sometimes the Human nose, nose. Vomiting can be ...
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Doxorubicin
Doxorubicin, sold under the brand name Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used together with other chemotherapy agents. Doxorubicin is given by injection into a vein. Common side effects include hair loss, bone marrow suppression, vomiting, rash, and inflammation of the mouth. Other serious side effects may include allergic reactions such as anaphylaxis, heart damage, tissue damage at the site of injection, radiation recall, and treatment-related leukemia. People often experience red discoloration of the urine for a few days. Doxorubicin is in the anthracycline and antitumor antibiotic family of medications. It works in part by interfering with the function of DNA. Doxorubicin was approved for medical use in the United States in 1974. It is on the World Health Organization's List of Essential Medicines. Versions th ...
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