New phosphoramidite reagents for the synthesis of oligonucleotides containing a cysteine residue useful in peptide conjugation.
The preparation is described of four 2-cyanoethyl-N,N-diisopropyl phosphoramidites of N-alpha-Fmoc-S-protected cysteine hydroxyalkyl amides. The phosphoramidites were used in solid-phase synthesis of 5'-cysteinyl oligonucleotides, useful intermediates in the preparation of peptide-oligonucleotide conjugates through reaction with a maleimide peptide or with a peptide thioester via "native ligation".
Stetsenko
D A
DA
Medical Research Council, Laboratory of Molecular Biology, Cambridge, UK.
Gait
M J
MJ
D001483:Base Sequence; D003545:Cysteine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013873:Thionucleotides / Q000737:chemistry*
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D010455:Peptides; D013873:Thionucleotides; D003545:Cysteine