Nucleocidin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02612 |
| CAS | 24751-69-7 |
| Molecular Weight | 364.31 |
| Molecular Formula | C10H13FN6O6S |
| Purity | >98% |
Online Inquiry
Description
Nucleocidin is originally isolated from Str. calvus T 3018 and it is mainly resistant to bacteria, mycoplasma and protozoa.
Specification
| Synonyms | 4'-Fluoro-5'-O-sulfamoyladenosine; Antibiotic T-3018; 4'-C-Fluoroadenosine 5'-sulfamate; NSC 521007 |
| Storage | Store at -20°C |
| IUPAC Name | [(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-fluoro-3,4-dihydroxyoxolan-2-yl]methyl sulfamate |
| Canonical SMILES | C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)(COS(=O)(=O)N)F)O)O)N |
| 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 |
| InChI Key | LTBCQBSAWAZBDF-MLTZYSBQSA-N |
Properties
| Appearance | White Crystalline |
| Antibiotic Activity Spectrum | mycoplasma |
| Boiling Point | 747.6°C at 760 mmHg |
| Melting Point | >190°C (dec) |
| Density | 2.23 g/cm3 |
Reference Reading
1. Identification of Genes Essential for Sulfamate and Fluorine Incorporation During Nucleocidin Biosynthesis
A R Ola Pasternak, Andreas Bechthold, David L Zechel Chembiochem. 2022 Aug 3;23(15):e202200140. doi: 10.1002/cbic.202200140. Epub 2022 May 24.
Nucleocidin is an adenosine derivative containing 4'-fluoro and 5'-O-sulfamoyl substituents. In this study, nucleocidin biosynthesis is examined in two newly discovered producers, Streptomyces virens B-24331 and Streptomyces aureorectus B-24301, which produce nucleocidin and related derivatives at titers 30-fold greater than S. calvus. This enabled the identification of two new O-acetylated nucleocidin derivatives, and a potential glycosyl-O-acetyltransferase. Disruption of nucJ, nucG, and nucI, within S. virens B-24331, specifying a radical SAM/Fe-S dependent enzyme, sulfatase, and arylsulfatase, respectively, led to loss of 5'-O-sulfamoyl biosynthesis, but not fluoronucleoside production. Disruption of nucN, nucK, and nucO specifying an amidinotransferase, and two sulfotransferases respectively, led to loss of fluoronucleoside production. Identification of S. virens B-24331 as a genetically tractable and high producing strain sets the stage for understanding nucleocidin biosynthesis and highlights the utility of using 16S-RNA sequences to identify alternative producers of valuable compounds in the absence of genome sequence data.
2. 4'-Fluoro-nucleosides and nucleotides: from nucleocidin to an emerging class of therapeutics
Phillip T Lowe, David O'Hagan Chem Soc Rev. 2023 Jan 3;52(1):248-276. doi: 10.1039/d2cs00762b.
The history and development of 4'-fluoro-nucleosides is discussed in this review. This is a class of nucleosides which have their origin in the discovery of the rare fluorine containing natural product nucleocidin. Nucleocidin contains a fluorine atom located at the 4'-position of its ribose ring. From its early isolation as an unexpected natural product, to its total synthesis and bioactivity assessment, nucleocidin has played a role in inspiring the exploration of 4'-fluoro-nucleosides as a privileged motif for nucleoside-based therapeutics.
3. Isolation of 5'- O-sulfamyladenosine and related 3'- O-β-glucosylated adenosines from the nucleocidin producer Streptomyces calvus
Xuan Feng, Davide Bello, David O'Hagan RSC Adv. 2021 Jan 28;11(10):5291-5294. doi: 10.1039/d1ra00235j.
The isolation of three adenosine based metabolites 6-8 from Streptomyces calvus is reported. The metabolites are structurally related to the fluorine containing antibiotic nucleocidin 1 and two recently identified glycosylated fluoroadenosines 2 and 3, however in this case the three metabolites do not contain a fluorine, suggesting that the biosynthetic enzymes to the fluorometabolites also process their non-fluorinated counterparts.
Recommended Products
| BBF-05862 | Epirubicin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
