Nucleocidin

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-dihydroxytetrahydrofuran-2-yl]methyl sulfamate
Identifiers
CAS Number	24751-69-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:166872
ChemSpider	65250
PubChem CID	72299
UNII	F5097NG7JT
InChI 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
SMILES c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@](O3)(COS(=O)(=O)N)F)O)O)N
Properties
Chemical formula	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). Infobox references

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 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 Streptomycesaurorectus. ^[6]

Biochemical relevance

The compound is capable of interrupting the synthesis of peptides. ^[7]

See also

• 4-Fluoro-L-threonine

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.