Desosamine
Chemical compound From Wikipedia, the free encyclopedia
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,[1][2] azithromycin, clarithroymcin, 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.[3] The biological action of the desosamine-based macrolide antibiotics is to inhibit the bacterial ribosomal protein synthesis.[4] These antibiotics which contain desosamine are widely used to cure bacterial-causing infections in human respiratory system, skin, muscle tissues, and urethra.
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| Names | |
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| IUPAC name
3,4,6-Trideoxy-3-(dimethylamino)-D-xylo-hexose | |
| Systematic IUPAC name
(2R,3S,5R)-3-(Dimethylamino)-2,5-dihydroxyhexanal | |
| Identifiers | |
3D model (JSmol) |
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| 2412240 | |
| ChEBI | |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H17NO3 | |
| Molar mass | 175.23 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Discovery
Although desosamine has been found in many macrolide antibiotics, the complete chemical structure of desosamine was not determined until 1962.[5] 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.[5]
Biosynthesis
Six enzymes are required for desosamine biosynthesis from TDP-glucose in Streptomyces venezuelae.[1][6] In addition to the required enzymes, there are eight important open reading frames known as the des regions, they are desI~desVIII, these eight frames are the necessary genes used in desosamine biosynthesis, among the 8 des regions, the desI gene implements C-4 Deoxygenation by the enzymatic activity of dehydrase. [7]
Degradation
Degradation of several of the aforementioned antibiotics yields the desosamine sugar. It is found in combination with the smaller macrolide rings, always attached at C-3 or C-5 of the aglycone. Alkaline degradation found the sugar to be a D-hexose derivative.[8] Glycosidic cleavage of methomycin produces aglycone methynolide and the basic sugar desosamine, whose structure had been determined by oxidative degradation to crotonaldehyde and by other experiments.[9]
Drug resistance
Macrolide antibiotics that contain desosamine as an amino sugar in their chemical structures sometimes encounter drug-resistant bacteria. The target-site modification can result in changing chemical structure of the antibiotics, for example, a methylation mutation, which will block the drug from normally functioning.[10]
See also
References
External links
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