2'-Hydrazine oligonucleotides: synthesis and efficient conjugation with aldehydes.
Oligodeoxyribonucleotides that contain a novel nucleoside, 2'-O-(2-hydrazinoethyl)uridine, were synthesized by sodium cyanoborohydride reduction of hydrazones formed from 2'-aldehyde oligonucleotides and FmocNHNH2 followed by ammonia deprotection. 2'-Hydrazine oligonucleotides were used successfully to obtain a series of conjugates with various aldehydes by hydrazone formation. The method was shown to be suitable for the preparation of oligonucleotide-peptide conjugates.
Zatsepin
Timofei S
TS
Department of Chemistry, M. V. Lomonossov Moscow State University, 1 Leninskie gory, Moscow 119992, Russia.
Stetsenko
Dmitry A
DA
Gait
Michael J
MJ
Oretskaya
Tatiana S
TS
D000447:Aldehydes / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry
C520198:2'-O-(2-hydrazinoethyl)uridine; D000447:Aldehydes; D006834:Hydrazines; D009838:Oligodeoxyribonucleotides; D014529:Uridine