Daunosamine
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Names | |||
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IUPAC names
Linear:(3S,4S,5S)-3-amino-4,5-dihydroxyhexanal
Pyranose: (3S,4S,5S)-4-amino-6-methyl-tetrahydropyran-2,5-diol | |||
Other names
3-Amino-2,3,6-trideoxy-L-lyxo-hexose
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Identifiers | |||
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3D model (JSmol)
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ChemSpider | |||
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |||
C6H13NO3 | |||
Molar mass | 147.174 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Daunosamine is a deoxy sugar and amino sugar of the hexosamine class.[1]
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.[2]
References
- ^ Grethe, Guenter; Mitt, Toomas; Williams, Thomas H; Uskokovic, Milan R (1983). "Synthesis of daunosamine". The Journal of Organic Chemistry. 48 (26): 5309–5315. doi:10.1021/jo00174a028.
- ^ Otten, S. L; Liu, X; Ferguson, J; Hutchinson, C. R (1995). "Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyl transferase involved in daunorubicin biosynthesis". Journal of Bacteriology. 177 (22): 6688–92. doi:10.1128/jb.177.22.6688-6692.1995. PMC 177529. PMID 7592454.
External links
- Daunosamine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
Categories:
- Chemical articles with multiple compound IDs
- Multiple chemicals in an infobox that need indexing
- Chemical articles with multiple CAS registry numbers
- Articles without EBI source
- Articles without KEGG source
- Articles without UNII source
- Articles with changed CASNo identifier
- Articles with changed ChemSpider identifier
- Articles with changed InChI identifier
- Articles containing unverified chemical infoboxes
- Chembox image size set
- Articles with short description
- Short description matches Wikidata
- Hexosamines
- Deoxy sugars