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A new approach has been devised for the synthesis of oligonucleotides containing 2'-deoxy-6-thioguanosine [d(s6G)]. The synthesis of oligonucleotides containing d(s6G) requires special protection and deprotection strategies to prevent the thione functionality from undergoing oxidation and hydrolysis. Previous attempted syntheses have neglected to address this problem. By using the cyanoethyl protecting group for the thione and phenoxyacetyl for the exocyclic amino group, it was possible to deprotect oligonucleotides with a mixture of sodium hydroxide and sodium hydrogen sulfide without any significant conversion of d(s6G) to deoxyguanosine. Application of this strategy will allow investigation of the structural as well as biological activity of d(s6G)-containing oligonucleotides.
M S Christopherson, and
A D Broom
February 1964,
Nature,
M S Christopherson, and
A D Broom
July 2018,
Bioorganic & medicinal chemistry,
M S Christopherson, and
A D Broom
March 2012,
Current protocols in nucleic acid chemistry,
M S Christopherson, and
A D Broom
August 2009,
Nucleosides, nucleotides & nucleic acids,
M S Christopherson, and
A D Broom
January 2003,
Nucleosides, nucleotides & nucleic acids,
M S Christopherson, and
A D Broom
February 1995,
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M S Christopherson, and
A D Broom
January 2005,
Nucleosides, nucleotides & nucleic acids,
M S Christopherson, and
A D Broom
October 1979,
Cancer research,
M S Christopherson, and
A D Broom
January 1999,
Nucleosides & nucleotides,
M S Christopherson, and
A D Broom
January 1993,
The Journal of organic chemistry,
