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desosamine
Sign in to saveAlso known as D-xylo-Hexose, 3,4,6-trideoxy-3-(dimethylamino)-
Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found in certain macrolide antibiotics (contain a high level of microbial resistance) such as the commonly prescribed erythromycin, azithromycin, clarithromycin, methymycin, narbomycin, oleandomycin, picromycin and roxithromycin. As the name suggests, these macrolide antibiotics contain a macrolide or lactone ring and they are attached to the ring desosamine which is crucial for bactericidal activity. The biological action of the desosamine-based macrolide antibiotics is to inhibit the bacterial ribosomal protein synthesis. These antibioti
In the Vinony graph
Within Vinony's link graph, desosamine is referenced by 5 other articles, and connects out to enzyme, digital object identifier and chemical formula.
It is catalogued under topics including Chembox image size set, Dimethylamino compounds and Diols.
Its subject is documented across 8 Wikipedia language editions.
Chemical data
- Formula
- C8H17NO3
- Molecular weight
- 175.23 g/mol
- IUPAC name
- (2R,3S,5R)-3-(dimethylamino)-2,5-dihydroxyhexanal
- SMILES
- C[C@H](C[C@@H]([C@H](C=O)O)N(C)C)O
- InChIKey
- VTJCSBJRQLZNHE-CSMHCCOUSA-N
- XLogP
- -0.7
- Polar surface area
- 60.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 175.120843
Show 3 more facts
- chemical formula
- C₈H₁₇NO₃
- isomeric SMILES
- C[C@H](C[C@@H]([C@H](C=O)O)N(C)C)O
- canonical SMILES
- CC(CC(C(C=O)O)N(C)C)O
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Discovery
- Biosynthesis
- Degradation
- Drug resistance
- See also
- References
- External links
Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found in certain macrolide antibiotics (contain a high level of microbial resistance) such as the commonly prescribed erythromycin, azithromycin, clarithromycin, methymycin, narbomycin, oleandomycin, picromycin and roxithromycin. As the name suggests, these macrolide antibiotics contain a macrolide or lactone ring and they are attached to the ring desosamine which is crucial for bactericidal activity. The biological action of the desosamine-based macrolide antibiotics is to inhibit the bacterial ribosomal protein synthesis. These antibiotics which contain desosamine are widely used to cure bacterial infections in human respiratory system, skin, muscle tissues, and urethra.
== Discovery == Although desosamine has been found in many macrolide antibiotics, the complete chemical structure of desosamine was not determined until 1962. Nuclear magnetic resonance spectroscopy data was used to establish the complete configuration of desosamine. The hydrogen atoms at the C1,C2,C3, and C5 positions are all found to be axial.
Excerpted from Wikipedia’s “desosamine” article, available under the CC BY-SA 4.0 licence.