Nucleocidin

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Nucleocidin
Names
IUPAC name
4′-Fluoroadenosine 5′-sulfamate
Systematic IUPAC name
[(2S,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-2-fluoro-3,4-dihydroxyoxan-2-yl]methyl sulfamate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C10H13FN6O6S/c11-10(1-22-24(13,20)21)6(19)5(18)9(23-10)17-3-16-4-7(12)14-2-15-8(4)17/h2-3,5-6,9,18-19H,1H2,(H2,12,14,15)(H2,13,20,21)/t5-,6+,9-,10-/m1/s1
    Key: LTBCQBSAWAZBDF-MLTZYSBQSA-N
  • c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@](O3)(COS(=O)(=O)N)F)O)O)N
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]

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 PMR and mass spectroscopy, 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]

See also

References

  1. ^ Bartholomé, Axel; Janso, Jeffrey E; Reilly, Usa; O'Hagan, David (2017). "Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus". Organic & Biomolecular Chemistry. 15 (1): 61–64. doi:10.1039/c6ob02291j. hdl:10023/12031. PMID 27845468.
  2. ^ Pasternak, Ola; Zechel, David (May 2022). "Identification of Genes Essential for Sulfamate and Fluorine Incorporation During Nucleocidin Biosynthesis". The FASEB Journal. 36 (S1): fasebj.2022.36.S1.R2700. doi:10.1096/fasebj.2022.36.S1.R2700. hdl:1974/30179. ISSN 0892-6638. PMID 35552629. S2CID 248654450.
  3. ^ Carvalho, Maria F.; Oliveira, Rui S. (2017-10-03). "Natural production of fluorinated compounds and biotechnological prospects of the fluorinase enzyme". Critical Reviews in Biotechnology. 37 (7): 880–897. doi:10.1080/07388551.2016.1267109. hdl:10400.22/13870. ISSN 0738-8551. PMID 28049355. S2CID 27301409.
  4. ^ Shuman, Dennis A.; Robins, Morris J.; Robins, Roland K. (June 1970). "Synthesis of Nucleoside Sulfamates Related to Nucleocidin". Journal of the American Chemical Society. 92 (11): 3434–3440. doi:10.1021/ja00714a035. ISSN 0002-7863. PMID 5422764 – via JACS.
  5. ^ Carvalho, Maria F.; Oliveira, Rui S (October 2017). "Natural Production of Fluorinated Compounds and Biotechnological Prospects of the Fluorinate Enzyme". Critical Reviews in Biotechnology. 37 (7): 880–897. doi:10.1080/07388551.2016.1267109. hdl:10400.22/13870. ISSN 0738-8551. PMID 28049355. S2CID 27301409.
  6. ^ Pasternak, Ola; Zechel, David (May 2022). "Identification of Genes Essential for Sulfamate and Fluorine Incorporation During Nucleocidin Biosynthesis". The FASEB Journal. 36 (S1): fasebj.2022.36.S1.R2700. doi:10.1096/fasebj.2022.36.S1.R2700. hdl:1974/30179. ISSN 0892-6638. PMID 35552629. S2CID 248654450.
  7. ^ Bloch, A.; Coutsogeorgopoulos, C. (1971-11-01). "Inhibition of protein synthesis by 5'-sulfamoyladenosine". Biochemistry. 10 (24): 4394–4398. doi:10.1021/bi00800a007. ISSN 0006-2960. PMID 4946919.


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