Nucleocidin

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Nucleocidin
Nucleocidin.svg
Names
Preferred 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[edit]

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[edit]

Nucleocidin is an antibiotic produced from Streptomyces calvus. Though toxic to mammals, it is able functions 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[edit]

Nucleocidin has anti-parasitic properties.[7] The compound is capable of interrupting the synthesis of peptides.[8]

See also[edit]

References[edit]

  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. 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. 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. ISSN 0892-6638. PMID 35552629. S2CID 248654450.
  7. ^ Dixit, Shailesh S.; Upadhayaya, Ram Shankar; Chattopadhyaya, Jyoti (2012). "New parasite inhibitors encompassing novel conformationally-locked 5′-acyl sulfamoyl adenosines". Organic & Biomolecular Chemistry. 10 (30): 6121. doi:10.1039/c2ob25879j. ISSN 1477-0520. PMID 22710960.
  8. ^ 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.