title: DNA or RNA oligonucleotide 2'-hydrazides for chemoselective click-type ligation with carbonyl compounds.
abstract: An efficient method for the synthesis of DNA or RNA oligonucleotide 2'-hydrazides is described. Fully deprotected oligonucleotides containing a hydrazide group at the 2'-position of a uridine residue were obtained by a novel two-step procedure: periodate cleavage of an oligonucleotide with 1,2-diol group followed by conversion of the aldehyde to hydrazide with an extended linker arm using a homobifunctional reagent succinic dihydrazide and NaBH(3)CN. The resulting oligonucleotide 2'-hydrazides were efficiently conjugated by a click-type reaction at acidic pH to aliphatic or aromatic aldehydes with or without NaBH(3)CN reduction to afford novel 2'-conjugates.
authors: Department of Chemistry, A. N. Belozersky Institute of Physico-Chemical Biology, M. V. Lomonossov Moscow State University, Leninskie Gory, Moscow, Russia.
authors: Elena A
authors: EA
authors: Khomyakova
authors: Eugeny M
authors: EM
authors: Zubin
authors: Igor P
authors: IP
authors: Smirnov
authors: Galina E
authors: GE
authors: Pozmogova
authors: Dmitry A
authors: DA
authors: Stetsenko
authors: Tatiana S
authors: TS
authors: Oretskaya
mesh_terms: D057930:Click Chemistry / Q000191:economics / Q000379:methods*; D004247:DNA / Q000138:chemical synthesis*; D006834:Hydrazines / Q000138:chemical synthesis*; D009841:Oligonucleotides / Q000138:chemical synthesis*; D012313:RNA / Q000138:chemical synthesis*; D013386:Succinates
chemical_list: D006834:Hydrazines; D009841:Oligonucleotides; D013386:Succinates; C063357:succinic dihydrazide; D012313:RNA; D004247:DNA