Synthesis and application of a novel, crystalline phosphoramidite monomer with thiol terminus, suitable for the synthesis of DNA conjugates.
A new, crystalline 5'-thiol modifier phosphoramidite monomer (3), suitable for DNA synthesis, has been prepared. This monomer has been built into an oligonucleotide using the standard protocol. After cleavage, purification and removal of the trityl group with Ag(+), a free 5'-thiol terminal oligonucleotide (15) has been obtained which was subsequently coupled to a cysteine derivative via a disulfide bridge to afford conjugate 16.
Kupihár
Z
Z
Department of Medicinal Chemistry, Dóm tér 8, University of Szeged, H-6720 Szeged, Hungary. kupi@ovrisc.mdche.u-szeged.hu
Schmél
Z
Z
Kele
Z
Z
Penke
B
B
Kovács
L
L
D002839:Chromans / Q000138:chemical synthesis* / Q000652:urine*; D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000031:analogs & derivatives / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000302:isolation & purification; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010421:Pentanoic Acids / Q000138:chemical synthesis* / Q000652:urine*; D021241:Spectrometry, Mass, Electrospray Ionization; D013438:Sulfhydryl Compounds / Q000737:chemistry*
C434334:5-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-2-methyl-pentanoic acid; D002839:Chromans; D004220:Disulfides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D010421:Pentanoic Acids; D013438:Sulfhydryl Compounds; C434331:phosphoramidite; D003545:Cysteine