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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) | |
ChEBI | |
ChemSpider | |
PubChem CID | |
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). |
Nucleocidin is a fluorine-containing nucleoside produced by Streptomyces calvus . [1]
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]
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 Streptomycesaurorectus. [6]
The compound is capable of interrupting the synthesis of peptides. [7]