Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill

Andrew J. Cummings; Francesco Ravalico; Kegan I. S.  McColgan-Bannon; Olga Eguaogie; P. Alain Elliott; Matthew R.  Shannon; Iris A.  Bermejo; Angus Dwyer; Amanda B. Maginty; James Mack; Joseph S. Vyle

doi:10.1080/15257770.2014.1001855

Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill

Andrew J. Cummings, Francesco Ravalico, Kegan I. S. McColgan-Bannon, Olga Eguaogie, P. Alain Elliott, Matthew R. Shannon, Iris A. Bermejo, Angus Dwyer, Amanda B. Maginty, James Mack, Joseph S. Vyle

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5 '-azido-5 '-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5mol% Cu(I) in the presence of a stabilizing ligand. 'Click' reactions using the monopropargylamides were also effected in the absence of added cuprous salts by the application of liquid assisted grinding (LAG) in metallic copper reaction vials. Specifically, high speed vibration ball milling (HSVBM) using a 3/32('') (2.38mm) diameter copper ball (62mg) at 60Hz overnight in the presence of ethyl acetate lead to complete consumption of the 5 '-azido nucleoside with clean conversion to the corresponding 1,3-triazole.

Original language	English
Pages (from-to)	361-370
Number of pages	10
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	34
Issue number	5
DOIs	https://doi.org/10.1080/15257770.2014.1001855
Publication status	Published - 15 Apr 2015

Keywords

TERMINAL ALKYNES
CLICK CHEMISTRY
SOLVENT-FREE
DNA
NANOPARTICLES
PROTECTION

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10.1080/15257770.2014.1001855

Synthesis of novel sugar analogues from levoglucosenone
Cummings, A. (Author), Sheldrake, G. (Supervisor), Jul 2019
Student thesis: Doctoral Thesis › Doctor of Philosophy

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Joseph Samuel Vyle
- j.vylequb.acuk
- School of Chemistry and Chemical Engineering - Lecturer
- Organic Synthesis and Chemical Biology
Person: Academic

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Cummings, A. J., Ravalico, F., McColgan-Bannon, K. I. S., Eguaogie, O., Elliott, P. A., Shannon, M. R., Bermejo, I. A., Dwyer, A., Maginty, A. B., Mack, J., & Vyle, J. S. (2015). Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill. Nucleosides, Nucleotides and Nucleic Acids, 34(5), 361-370. https://doi.org/10.1080/15257770.2014.1001855

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title = "Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill",

abstract = "Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5 '-azido-5 '-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5mol% Cu(I) in the presence of a stabilizing ligand. 'Click' reactions using the monopropargylamides were also effected in the absence of added cuprous salts by the application of liquid assisted grinding (LAG) in metallic copper reaction vials. Specifically, high speed vibration ball milling (HSVBM) using a 3/32('') (2.38mm) diameter copper ball (62mg) at 60Hz overnight in the presence of ethyl acetate lead to complete consumption of the 5 '-azido nucleoside with clean conversion to the corresponding 1,3-triazole.",

keywords = "TERMINAL ALKYNES, CLICK CHEMISTRY, SOLVENT-FREE, DNA, NANOPARTICLES, PROTECTION",

author = "Cummings, {Andrew J.} and Francesco Ravalico and McColgan-Bannon, {Kegan I. S.} and Olga Eguaogie and Elliott, {P. Alain} and Shannon, {Matthew R.} and Bermejo, {Iris A.} and Angus Dwyer and Maginty, {Amanda B.} and James Mack and Vyle, {Joseph S.}",

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doi = "10.1080/15257770.2014.1001855",

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Cummings, AJ, Ravalico, F, McColgan-Bannon, KIS, Eguaogie, O, Elliott, PA, Shannon, MR, Bermejo, IA, Dwyer, A, Maginty, AB, Mack, J & Vyle, JS 2015, 'Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill', Nucleosides, Nucleotides and Nucleic Acids, vol. 34, no. 5, pp. 361-370. https://doi.org/10.1080/15257770.2014.1001855

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T1 - Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill

AU - Cummings, Andrew J.

AU - Ravalico, Francesco

AU - McColgan-Bannon, Kegan I. S.

AU - Eguaogie, Olga

AU - Elliott, P. Alain

AU - Shannon, Matthew R.

AU - Bermejo, Iris A.

AU - Dwyer, Angus

AU - Maginty, Amanda B.

AU - Mack, James

AU - Vyle, Joseph S.

PY - 2015/4/15

Y1 - 2015/4/15

N2 - Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5 '-azido-5 '-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5mol% Cu(I) in the presence of a stabilizing ligand. 'Click' reactions using the monopropargylamides were also effected in the absence of added cuprous salts by the application of liquid assisted grinding (LAG) in metallic copper reaction vials. Specifically, high speed vibration ball milling (HSVBM) using a 3/32('') (2.38mm) diameter copper ball (62mg) at 60Hz overnight in the presence of ethyl acetate lead to complete consumption of the 5 '-azido nucleoside with clean conversion to the corresponding 1,3-triazole.

AB - Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5 '-azido-5 '-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5mol% Cu(I) in the presence of a stabilizing ligand. 'Click' reactions using the monopropargylamides were also effected in the absence of added cuprous salts by the application of liquid assisted grinding (LAG) in metallic copper reaction vials. Specifically, high speed vibration ball milling (HSVBM) using a 3/32('') (2.38mm) diameter copper ball (62mg) at 60Hz overnight in the presence of ethyl acetate lead to complete consumption of the 5 '-azido nucleoside with clean conversion to the corresponding 1,3-triazole.

KW - TERMINAL ALKYNES

KW - CLICK CHEMISTRY

KW - SOLVENT-FREE

KW - DNA

KW - NANOPARTICLES

KW - PROTECTION

U2 - 10.1080/15257770.2014.1001855

DO - 10.1080/15257770.2014.1001855

M3 - Article

SN - 1525-7770

VL - 34

SP - 361

EP - 370

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 5

ER -

Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill

Abstract

Keywords

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Student theses

Synthesis of novel sugar analogues from levoglucosenone

Profiles

Joseph Samuel Vyle

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