Stereocontrolled synthesis and nuclear magnetic resonance analysis of boranophosphate/phosphate chimeric oligonucleotides
Kiyoshi Kakuta, Taiichi Sakamoto, Hajime Sato, Kazuki Sato, Takeshi Wada
TL;DR
This paper presents a method for creating and analyzing chimeric DNA-like molecules with precise stereochemistry using NMR techniques.
Contribution
A stereoselective synthesis method and NMR analysis for boranophosphate/phosphate chimeric oligonucleotides with retained stereochemistry.
Findings
Dimer building blocks with stereopure boranophosphotriester linkages enabled synthesis of PB/PO chimeric ODNs.
NOESY experiments confirmed the stereochemistry of PB linkages in oligomers.
Stereochemistry was retained during solid-phase synthesis without loss of stereopurity.
Abstract
This report describes the stereoselective synthesis of boranophosphate/phosphate (PB/PO) chimeric oligodeoxynucleotides (ODNs) and the nuclear magnetic resonance (NMR) analysis of oligomers containing PB linkages. This stereoselective synthesis involved dimer building blocks containing highly stereopure boranophosphotriester linkages, which enabled the synthesis of PB/PO chimeric ODNs via the standard phosphoramidite method. The stereochemistry of dinucleoside and trinucleoside PBs was confirmed by nuclear Overhauser effect spectroscopy (NOESY) experiments. In the NOESY experiments, the stereochemistry was determined from the correlation of the protons of the borane (BH3) group with those of neighbouring 2'-deoxyribose moieties or nucleobases. Thus, the stereochemistry of the PB linkages within the oligomer was determined, and the stereopurity was also confirmed. A PB linkage was…
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Taxonomy
TopicsDNA and Nucleic Acid Chemistry · Advanced biosensing and bioanalysis techniques · Neurogenetic and Muscular Disorders Research