2-Fluoroadenine

2-Fluoroadenine (2-FA) is a toxic adenine antimetabolite which can be used in laboratory biological research for counterselection of wildtype bacterial[3] or eukaryotic (i.e. animals,[4] yeast,[5] plants,[6] diatoms,[7] brown algae[8]) APT (adenine phosphoribosyltransferase) genes. Therefore, knockouts or mutants for APT, which are resistant to 2-FA, can be selected.

2-Fluoroadenine
Names
IUPAC name
2-Fluoro-7H-purin-6-amine
Other names
2-FA
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.152.774
EC Number
  • 624-159-6
UNII
  • InChI=1S/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)
    Key: WKMPTBDYDNUJLF-UHFFFAOYSA-N
  • C1=NC2=NC(=NC(=C2N1)N)F
Properties
C5H4FN5
Molar mass 153.120 g·mol−1
< 0.5 mM[1]
Solubility >=10 mM in DMSO
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Kayushin, Alexey L.; Tokunova, Julia A.; Fateev, Ilja V.; Arnautova, Alexandra O.; Berzina, Maria Ya.; Paramonov, Alexander S.; Lutonina, Olga I.; Dorofeeva, Elena V.; Antonov, Konstantin V.; Esipov, Roman S.; Mikhailopulo, Igor A.; Miroshnikov, Anatoly I.; Konstantinova, Irina D. (2021-04-07). "Radical Dehalogenation and Purine Nucleoside Phosphorylase E. coli: How Does an Admixture of 2′,3′-Anhydroinosine Hinder 2-fluoro-cordycepin Synthesis". Biomolecules. MDPI AG. 11 (4): 539. doi:10.3390/biom11040539. ISSN 2218-273X. PMC 8067715. PMID 33917025.
  2. "2-Fluoroadenine". pubchem.ncbi.nlm.nih.gov. Retrieved 4 May 2022.
  3. Riley, Lauren A.; Guss, Adam M. (2021-01-25). "Approaches to genetic tool development for rapid domestication of non-model microorganisms". Biotechnology for Biofuels. Springer Science and Business Media LLC. 14 (1): 30. doi:10.1186/s13068-020-01872-z. ISSN 1754-6834. PMC 7830746. PMID 33494801.
  4. Schaff, D A; Jarrett, R A; Dlouhy, S R; Ponniah, S; Stockelman, M; Stambrook, P J; Tischfield, J A (1990). "Mouse transgenes in human cells detect specific base substitutions". Proceedings of the National Academy of Sciences of the United States of America. 87 (21): 8675–8679. Bibcode:1990PNAS...87.8675S. doi:10.1073/pnas.87.21.8675. PMC 55020. PMID 2236079.
  5. Sahota, Amrik; Ranjekar, Prabhakar K.; Alfonzo, Juan; Lewin, Alfred S.; Taylor, Milton W. (1987). "Mutants of Saccharomyces cerevisiae deficient in adenine phosphoribosyltransferase". Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. Elsevier BV. 180 (1): 81–87. doi:10.1016/0027-5107(87)90069-8. ISSN 0027-5107. PMID 3306356.
  6. Schaff, Dennis A. (1994). "The adenine phosphoribosyltransferase (APRT) selectable marker system". Plant Science. Elsevier BV. 101 (1): 3–9. doi:10.1016/0168-9452(94)90159-7. ISSN 0168-9452.
  7. Serif, Manuel; Dubois, Gwendoline; Finoux, Anne-Laure; Teste, Marie-Ange; Jallet, Denis; Daboussi, Fayza (2018-09-25). "One-step generation of multiple gene knock-outs in the diatom Phaeodactylum tricornutum by DNA-free genome editing". Nature Communications. Springer Science and Business Media LLC. 9 (1): 3924. Bibcode:2018NatCo...9.3924S. doi:10.1038/s41467-018-06378-9. ISSN 2041-1723. PMC 6156588. PMID 30254261.
  8. Badis, Yacine; Scornet, Delphine; Harada, Minori; Caillard, Céline; Godfroy, Olivier; Raphalen, Morgane; Gachon, Claire M. M.; Coelho, Susana M.; Motomura, Taizo; Nagasato, Chikako; Cock, J. Mark (2021-07-10). "Targeted CRISPR‐Cas9‐based gene knockouts in the model brown alga Ectocarpus" (PDF). New Phytologist. Wiley. 231 (5): 2077–2091. doi:10.1111/nph.17525. ISSN 0028-646X. PMID 34076889. S2CID 235295486.
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