Stereocontrolled synthesis of oligoribonucleoside phosphorothioates by an oxazaphospholidine approach.
Oligoribonucleoside phosphorothioates (PS-ORNs) stereodefined at the phosphorus atoms were synthesized on solid support. Thermal denaturating experiments of the resultant PS-ORNs showed that a backbone consisting of (Sp)-PS-linkages as well as stereorandom PS-linkages had an unexpectedly large destabilizing effect on a PS-ORN-ORN duplex, whereas a backbone consisting of (Rp)-PS-linkages slightly stabilized a duplex.
Oka
Natsuhisa
N
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan.
Kondo
Tomoaki
T
Fujiwara
Satoshi
S
Maizuru
Yukihiro
Y
Wada
Takeshi
T
D008958:Models, Molecular; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010710:Phosphates; D054735:Phosphorothioate Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013816:Thermodynamics
C470122:(1,3,2)oxazaphospholidine; D010080:Oxazoles; D010710:Phosphates; D054735:Phosphorothioate Oligonucleotides; C035638:thiophosphoric acid