Mechanochemistry of nucleosides, nucleotides and related materials

Olga Eguaogie,
Joseph S. Vyle,
Patrick F. Conlon,
Manuela A. Gîlea and
Yipei Liang

Review
Published 27 Apr 2018

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1. Graphical Abstract
2. Figure 1: Examples of equipment used to perform mechanochemistry on nucleoside and nucleotide substrates (not...
  
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3. Figure 2: Ganciclovir.
  
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4. Scheme 1: Nucleoside tritylation effected by hand grinding in a heated mortar and pestle.
  
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5. Scheme 2: Persilylation of ribonucleoside hydroxy groups (and in situ acylation of cytidine) in a MBM.
  
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6. Scheme 3: Nucleoside amine and carboxylic acid Boc protection using an improvised attritor-type mill.
  
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7. Scheme 4: Nucleobase Boc protection via transient silylation using an improvised attritor-type mill.
  
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8. Scheme 5: Chemoselective N-acylation of an aminonucleoside using LAG in a MBM.
  
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9. Scheme 6: Azide–alkyne cycloaddition reactions performed in a copper vessel in a MBM.
  
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10. Figure 3: a) Custom-machined copper vessel and zirconia balls used to perform CuAAC reactions (showing: upper...
  
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11. Scheme 7: Thiolate displacement reactions of nucleoside derivatives in a MBM.
  
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12. Scheme 8: Selenocyanate displacement reactions of nucleoside derivatives in a MBM.
  
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13. Scheme 9: Nucleobase glycosidation reactions and subsequent deacetylation performed in a MBM.
  
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14. Scheme 10: Regioselective phosphorylation of nicotinamide riboside in a MBM.
  
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15. Scheme 11: Preparation of nucleoside phosphoramidites in a MBM using ionic liquid-stabilised chlorophosphorami...
  
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16. Scheme 12: Preparation of a nucleoside phosphite triester using LAG in a MBM.
  
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17. Scheme 13: Internucleoside phosphate coupling linkages in a MBM.
  
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18. Scheme 14: Preparation of ADPR analogues using in a MBM.
  
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19. Scheme 15: Synthesis of pyrophosphorothiolate-linked dinucleoside cap analogues in a MBM to effect hydrolytic ...
  
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20. Figure 4: Early low temperature mechanised ball mill as described by Mudd et al. – adapted from reference [78].
  
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21. Scheme 16: Co-crystal grinding of alkylated nucleobases in an amalgam mill (N.B. no frequency was recorded in ...
  
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22. Figure 5: Materials used to prepare a smectic phase.
  
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23. Figure 6: Structures of 5-fluorouracil (5FU) and nucleoside analogue prodrugs subject to mechanochemical co-c...
  
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24. Scheme 17: Preparation of DNA-SWNT complex in a MBM.
  
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