Enzymatic resolution and base pairing properties of D- and L-cyclohexenyl nucleic acids (CeNA).
An enzymatic transesterification reaction afforded large scale resolution of the cyclohexenol precursor needed for preparation of both series of CeNA building blocks. CeNA oligos of "D-like" chirality display a strong and selective interaction with RNA, while preserving RNase H activity, and therefore have potential as antisense constructs. CeNAs of opposite chirality form a self-pairing system on their own.
Gu
Ping
P
Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, Leuven, Belgium.
Schepers
Guy
G
Griebel
Carsten
C
Rozenski
Jef
J
Gais
Hans-Joachim
HJ
Herdewijn
Piet
P
Van Aerschot
Arthur
A
D020137:Base Pair Mismatch; D020029:Base Pairing; D004247:DNA / Q000737:chemistry; D006868:Hydrolysis; D008956:Models, Chemical; D009690:Nucleic Acid Conformation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry; D016376:Oligonucleotides, Antisense / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D016914:Ribonuclease H / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D009692:Nucleic Acid Heteroduplexes; D009696:Nucleic Acids; D009841:Oligonucleotides; D016376:Oligonucleotides, Antisense; D012313:RNA; D004247:DNA; D016914:Ribonuclease H