A simple method for the solid phase synthesis of oligodeoxynucleotides containing O4-alkylthymine | Zendy

YaoZhong Xu | Zendy; Peter Swann | Zendy

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A simple method for the solid phase synthesis of oligodeoxynucleotides containing O⁴-alkylthymine

Author(s) -

YaoZhong Xu,

Peter Swann

Publication year - 1990

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/18.14.4061

Subject(s) - phosphoramidite , oligomer , guanine , thymine , oligonucleotide , monomer , alkoxide , alkyl , cytosine , biology , dna , oligonucleotide synthesis , stereochemistry , protecting group , solid phase synthesis , combinatorial chemistry , nucleotide , biochemistry , polymer chemistry , chemistry , organic chemistry , polymer , peptide , gene , catalysis

A route to prepare the cyanoethyl-phosphoramidite monomer of O4-alkylthymine and a method for the routine solid-phase synthesis of oligodeoxynucleotides containing O4-alkylthymine are described. This method has been used to make DNA sequences up to 48 bases in length. The amino function of the adenine and guanine in the sequence were protected with the phenoxyacetyl group, and that of cytosine with the isobutyryl group. The phosphodiesters were protected with the cyanoethyl group. This allowed complete deprotection of the oligomer with alkoxide ions (methanol/1,8- diazabicyclo[5.4.0]undec-7-ene (DBU) for the oligomers containing O4-methylthymine, or ethanol/DBU for those containing O4-ethylthymine) thus avoiding the use of ammonia which is known to attack the O4-alkylthymine to form 5-methylcytosine. There was no detectable loss of the alkyl group to form thymine.

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