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Fluoro-Ribo-nucleoside triphosphates (19F rNTPs)

 

Fluorine labeling is a versatile and powerful tool for NMR structural investigation of nucleic acids. The fluorine nucleus offers several attractive properties for NMR spectroscopy: high NMR sensitivity (0.83 of 1H), 100% natural abundance, and a chemical shift that responds to its local chemical environment. In addition, fluorine’s virtual absence in biological systems enables measurements that are free of background signals making it an ideal candidate for in vivo NMR applications.

 

 

19F-13C labelling results in very favourable spectroscopic behaviour

 

Recently, Haribabu Arthanari and co-workers showed that an aromatic labeling scheme with a [19F-13C] spin pair has a very favourable spectroscopic behaviour in an NMR-TROSY experiment alleviating the size problem in nucleic acid NMR.

Figure_1_Sequence_and_NMR_TROSY_Date_Fluoro_rNTPs

The figure [1] shows the labelling patterns and the NMR-TROSY spectra at 25°C and at 0°C of Heron hepatitis B virus (hHBV) RNA with [6-D, 5-19F, 5-13C] uridine labels (highlighted in green) on the left and the [5-D, 6-13C] uridine labels on the right (highlighted in brown).

Both stable isotope labelling schemes gave well resolved correlation peaks at 25°C. At 0°C however, when the slowed down molecular mobility leads to a higher molecular weight like behavior, the superior spectral properties of the 19F/13C spin pair is manifested.

 

Conclusion of Haribabu Arthanaris study:

All five [6-D, 5-19F, 5-13C]-U labels were observed,
but only two of five 1H-13C uridine resonances were found.

 

The favorable spectral behaviour of labelled fluorine presents new opportunities for characterizing the structure, dynamics, and interactions of nucleic acids with the help of appropriate fluorine NMR hardware.

 

 

Silantes offers a range of 19F-labelled rNTP standards

Silantes offers suitable isotope labelled rNTP standards for your fluorine NMR project: (please see at the bottom of this page)

 

 


[1] Nußbaumer, Felix, Raphael Plangger, Manuel Roeck, and Christoph Kreutz. "Aromatic 19F–13C TROSY—[19F, 13C]‐Pyrimidine Labeling for NMR Spectroscopy of RNA." Angewandte Chemie (International Ed.) 59.39 (2020): 17062-7069.

Further references: 

  1. Synthesis of 5-fluoropyrimidine nucleotides as sensitive NMR probes of RNA structure. Hennig M, Scott LG, Sperling E, Bermel W, Williamson JR. J Am Chem Soc. 2007 Dec 5;129(48):14911-21. doi: 10.1021/ja073825i.
  2. Enzymatic synthesis and 19F NMR studies of 2-fluoroadenine-substituted RNA. Scott LG, Geierstanger BH, Williamson JR, Hennig M. J Am Chem Soc. 2004 Sep 29;126(38):11776-7. doi: 10.1021/ja047556
  3. Sochor, F., R. Silvers, D. Müller, C. Richter, B. Fürtig, and H. Schwalbe. "19F-labeling of the Adenine H2-site to Study Large RNAs by NMR Spectroscopy." Journal of Biomolecular NMR 64.1 (2015): 63-74. Web.
  4. Aromatic 19F-13C TROSY: a background-free approach to probe biomolecular structure, function, and dynamics. Boeszoermenyi A, Chhabra S, Dubey A, Radeva DL, Burdzhiev NT, Chanev CD, Petrov OI, Gelev VM, Zhang M, Anklin C, Kovacs H, Wagner G, Kuprov I, Takeuchi K, Arthanari H. Nat Methods. 2019 Apr;16(4):333-340. doi: 10.1038/s41592-019-0334-x.
  5. Solution NMR readily reveals distinct structural folds and interactions in doubly 13C- and 19F-labeled RNAs. Becette OB, Zong G, Chen B, Taiwo KM, Case DA, Dayie TK. Sci Adv. 2020 Oct 7;6(41):eabc6572. doi: 10.1126/sciadv.abc6572.

 


Related topics: Custom enzymatical oligo-synthesis service | Custom chemical oligo-synthesis service


 

 

 


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Product no.: 121903701

Synonym:

- 19F2 rATP Li2-salt

- 2-Flouro-adenosine-5'-triphosphate, Lithium-Salt

- 2-Flouro-ATP

- 2F-ATP


Chemical formula: C10H1519FN5O13P3

Isotopic enrichment > 98 atom %

Chemical purity > 95 %

$1,820.00 / 25 mg *

Please contact our customer service for information on availability and delivery time at
webshop@silantes.com

Product no.: 121903704

Synonym:

- 19F5 rUTP Li2-salt

- 5-Flouro-uridine-5'-triphophate, Lithium-Salt

- 5-Fluoro-UTP

- 5F-UTP


Chemical formula: C9H1419FN2O15P3

Isotopic enrichment > 98 atom %

Chemical purity > 95 %

$1,820.00 / 25 mg *

Please contact our customer service for information on availability and delivery time at
webshop@silantes.com

Product no.: 121923601

Synonym:

- 19F2 13C2 rATP Li2-salt

- 2-13C-2-Fluoro-adenosine-5'-triphophate, Lithium-Salt

- 2-13C-2-Fluoro-ATP

- 2-13C-2F-ATP


Chemical formula: C913CH1519FN5O13P3

Isotopic enrichment > 98 atom %

Chemical purity > 95 %

$1,740.00 / 10 mg *

Please contact our customer service for information on availability and delivery time at
webshop@silantes.com

Product no.: 121923701

Synonym:

- 19F2 13C2 rATP Li2-salt

- 2-13C-2-Fluoro-adenosine-5'-triphophate, Lithium-Salt

- 2-13C-2-Fluoro-ATP

- 2-13C-2F-ATP


Chemical formula: C913CH1519FN5O13P3

Isotopic enrichment > 98 atom %

Chemical purity > 95 %

$3,410.00 / 25 mg *

Please contact our customer service for information on availability and delivery time at
webshop@silantes.com

Product no.: 121943604

Synonym:

- 19F5 2H6 13C5 rUTP Li2-salt

- 5-13C-6-2H-5-Fluoro-uridine-5'-trisphophate, Lithium-Salt

- 5-13C-6-2H-5-Fluoro-UTP

- 5-13C-6-2H-5F-UTP


Chemical formula: C813CH13D19FN2O15P3

Isotopic enrichment > 98 atom %

Chemical purity > 95 %

$3,480.00 / 10 mg *

Please contact our customer service for information on availability and delivery time at
webshop@silantes.com

Product no.: 121943704

Synonym:

- 19F5 2H6 13C5 rUTP Li2-salt

- 5-13C-6-2H-5-Fluoro-uridine-5'-trisphophate, Lithium-Salt

- 5-13C-6-2H-5-Fluoro-UTP

- 5-13C-6-2H-5F-UTP


Chemical formula: C813CH13D19FN2O15P3

Isotopic enrichment > 98 atom %

Chemical purity > 95 %

$3,410.00 / 25 mg *

Please contact our customer service for information on availability and delivery time at
webshop@silantes.com

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