Incorporation of side-chain groups of basic amino acids into oligonucleotides via the 2'-position of uridine.
Certain amino acids and short peptides are known to act as enhancers of ribozyme-mediated RNA cleavage at low concentration of magnesium ion. Thus, covalent conjugates of oligonucleotides and some amino acids may have a potential for development as sequence-specific artificial ribonucleases. Here we would like to report an incorporation of basic amino acids, lysine and histidine, into oligonucleotides at the 2'-position of a uridine residue. The approach involves the 2'-O-alkylation and attachment of the corresponding amino acid by the alpha-amino group through a urethane-type linker.
Zubin
Eugeny M
EM
Chemistry Department, M. V. Lomonossov Moscow State University, 1 Leninskie Gory, Moscow 119992, Russia.
Stetsenko
Dmitry A
DA
Kachalova
Anna V
AV
Gait
Michael J
MJ
Oretskaya
Tatiana S
TS
D024361:Amino Acids, Basic / Q000737:chemistry*; D006639:Histidine / Q000737:chemistry; D008239:Lysine / Q000737:chemistry; D009841:Oligonucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D014529:Uridine / Q000737:chemistry*
D024361:Amino Acids, Basic; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D006639:Histidine; D008239:Lysine; D014529:Uridine