Concepedia

Adjustment of the <i>γ</i> Dihedral Angle of an Oligonucleotide P3′→N5′ Phosphoramidate Enhances Its Binding Affinity towards Complementary Strands

Satoshi Obika, Mitsuaki Sekiguchi, Somjing Roongjang, Takeshi Imanishi

Angewandte Chemie International Edition · 2005 · 12 citations · 18 references

DOI

Concepts

Abstract

Bridge to the right angle: A methylene bridge between the C3′ and N5′ atoms restricts the γ dihedral angle of an oligonucleotide P3′→N5′ phosphoramidate within the +sc orientation (see scheme), which improves duplex-forming ability and accelerates hydrolytic cleavage.

References

18

Synthesis of 2′-O,4′-C-methyleneuridine and -cytidine. Novel bicyclic nucleosides having a fixed C3, -endo sugar puckering

Satoshi Obika, Daishu Nanbu, Yoshiyuki Hari et al. · Tetrahedron Letters · 1997 · 601 citations

, , +13

Dinitrogen Reduction by Tm(II), Dy(II), and Nd(II) with Simple Amide and Aryloxide Ligands

William J. Evans, G. Zucchi, Joseph W. Ziller · Journal of the American Chemical Society · 2002 · 226 citations

, , +7

Efficient activation of nucleoside phosphoramidites with 4,5- dicyanoimidazole during oligonucleotide synthesis

Chandra Vargeese · Nucleic Acids Research · 1998 · 132 citations · Full text

, , +13

Nucleic‐Acid Analogues with Constraint Conformational Flexibility in the Sugar‐Phosphate Backbone (‘Bicyclo‐DNA’). Part 1. Preparation of (3<i>S</i>,5′<i>R</i>)‐2′‐Deoxy‐3′,5′‐ethano‐αβ‐<scp>D</scp>‐ribonucleosides (‘Bicyclonucleosides’)

Markus Tarköy, Martin H. Bolli, W. Bernd Schweizer et al. · Helvetica Chimica Acta · 1993 · 128 citations

, , +17

Nonaqueous oxidation of nucleoside phosphites to the phosphates

Yoshihiro Hayakawa, Mineto Uchiyama, Ryōji Noyori · Tetrahedron Letters · 1986 · 116 citations

, , +9