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On-demand synthesis of phosphoramidites

Author

Listed:
  • Alexander F. Sandahl

    (Aarhus University)

  • Thuy J. D. Nguyen

    (Aarhus University)

  • Rikke A. Hansen

    (Aarhus University)

  • Martin B. Johansen

    (Aarhus University)

  • Troels Skrydstrup

    (Aarhus University
    Aarhus University)

  • Kurt V. Gothelf

    (Aarhus University
    Aarhus University)

Abstract

Automated chemical synthesis of oligonucleotides is of fundamental importance for the production of primers for the polymerase chain reaction (PCR), for oligonucleotide-based drugs, and for numerous other medical and biotechnological applications. The highly optimised automised chemical oligonucleotide synthesis relies upon phosphoramidites as the phosphate precursors and one of the drawbacks of this technology is the poor bench stability of phosphoramidites. Here, we report on the development of an on-demand flow synthesis of phosphoramidites from their corresponding alcohols, which is accomplished with short reaction times, near-quantitative yields and without the need of purification before being submitted directly to automated oligonucleotide synthesis. Sterically hindered as well as redox unstable phosphoramidites are synthesised using this methodology and the subsequent couplings are near-quantitative for all substrates. The vision for this technology is direct integration into DNA synthesisers thereby omitting manual synthesis and storage of phosphoramidites.

Suggested Citation

  • Alexander F. Sandahl & Thuy J. D. Nguyen & Rikke A. Hansen & Martin B. Johansen & Troels Skrydstrup & Kurt V. Gothelf, 2021. "On-demand synthesis of phosphoramidites," Nature Communications, Nature, vol. 12(1), pages 1-7, December.
  • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-22945-z
    DOI: 10.1038/s41467-021-22945-z
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    Cited by:

    1. Nazarii Sabat & Andreas Stämpfli & Steven Hanlon & Serena Bisagni & Filippo Sladojevich & Kurt Püntener & Marcel Hollenstein, 2024. "Template-dependent DNA ligation for the synthesis of modified oligonucleotides," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    2. Nils J. H. Averesch & Aaron J. Berliner & Shannon N. Nangle & Spencer Zezulka & Gretchen L. Vengerova & Davian Ho & Cameran A. Casale & Benjamin A. E. Lehner & Jessica E. Snyder & Kevin B. Clark & Lew, 2023. "Microbial biomanufacturing for space-exploration—what to take and when to make," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    3. Chen, Qi & Duan, Yongrui, 2023. "Impact of information disclosure on global supply chain greenwashing: Is more information transparency always better?," Transportation Research Part E: Logistics and Transportation Review, Elsevier, vol. 178(C).

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