Nucleocidin
Chemical compound
From Wikipedia, the free encyclopedia
Nucleocidin is a fluorine-containing nucleoside produced by Streptomyces calvus.[1]
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| Names | |
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| IUPAC name
4′-Fluoroadenosine 5′-sulfamate | |
| Systematic IUPAC name
[(2S,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-2-fluoro-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| UNII | |
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| Properties | |
| C10H13FN6O6S | |
| Molar mass | 364.31 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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Chemical structure
Nucleocidin stems from the ribonucleoside adenosine[2] - is unique because it possess two rare functional groups: a fluorine atom and a sulfamyl ester [3]
During 1968 the attempts to identify nucleocidin were made and at that time it was assigned to a structure of a 9-adenyl-4' -sulfamoyloxypentofuranoside, which was mainly based on experiments from NMR and mass spectrometry, as well as testing in chemical reactions. It was ultimately proven to have a structure of a 4' -fluoro-5' -O-sulphamoyladenosine.[4]
Microbiological origin
Nucleocidin is an antibiotic produced from Streptomyces calvus. Though toxic to mammals, it is able to function against bacteria both gram negative gram positive. It may be used against trypanosomes.[5]
Though commonly known to be produced by Streptomyces calvus, nucleocidin is produced in greater yield by Streptomyces virens and Streptomyces aurorectus.[6]
Biochemical relevance
The compound is capable of interrupting the synthesis of peptides.[7]