Solid-phase synthesis of oligodeoxynucleotides containing N4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine moieties.
An efficient route for the synthesis of the phosphoramidite derivative of 5-methylcytosine bearing a tert-butylsulfanyl group protected thiol is described. This building block is used for the preparation of oligonucleotides carrying a thiol group at the nucleobase at the internal position of a DNA sequence. The resulting thiolated oligonucleotides are useful intermediates to generate oligonucleotide conjugates carrying molecules of interest at internal positions of a DNA sequence.
Pérez-Rentero
Sónia
S
Institute for Research in Biomedicine Barcelona, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Institute for Advanced Chemistry of Catalonia IQAC, CSIC, Baldiri Reixac 10, E-08028 Barcelona, Spain. sonia.perez@irbbarcelona.org
Garibotti
Alejandra V
AV
Eritja
Ramón
R
D044503:5-Methylcytosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D001483:Base Sequence; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000235:genetics; D012996:Solutions; D020122:tert-Butylhydroperoxide / Q000737:chemistry
D005456:Fluorescent Dyes; C553807:N4-(2-(t-butyldisulfanyl)ethyl)-5-methylcytosine; D009838:Oligodeoxyribonucleotides; D012996:Solutions; D044503:5-Methylcytosine; D020122:tert-Butylhydroperoxide; D007455:Iodine