(R)-2,4-Dihydroxybutyramide seco-pseudonucleosides: new versatile homochiral synthons for synthesis of modified oligonucleotides.
[reaction: see text] Two series of seco-pseudonucleoside synthons were synthesized from (R)-(+)-alpha-hydroxy-gamma-butyrolactone and (R)-(-)-pantolactone by aminolysis, side-chain protection, dimethoxytritylation, and phosphitylation or solid-phase attachment. The phosphoramidites and solid supports were used in automated DNA synthesis to prepare oligonucleotides modified with one or more 2,4-dihydroxybutyramide units bearing side-chain reporter groups. These new oligonucleotide modification reagents allow the introduction of a label into any desired position within an oligonucleotide chain during solid-phase assembly.
Dioubankova
Natalia N
NN
MRC Laboratory of Molecular Biology, Hills Road, Cambridge CB2 2QH, UK.
Malakhov
Andrey D
AD
Stetsenko
Dmitry A
DA
Korshun
Vladimir A
VA
Gait
Michael J
MJ
D000577:Amides / Q000737:chemistry; D001483:Base Sequence; D020650:Combinatorial Chemistry Techniques / Q000295:instrumentation; D004355:Drug Stability; D015335:Molecular Probes / Q000138:chemical synthesis; D009691:Nucleic Acid Denaturation; D009705:Nucleosides / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis*; D017905:Phosphites / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D000577:Amides; D015335:Molecular Probes; D009705:Nucleosides; D009841:Oligonucleotides; D017905:Phosphites; C006866:butyramide