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

• Published in: Angewandte Chemie (International ed.) Vol. 44; no. 13; pp. 1944 - 1947
• Main Authors: Obika, Satoshi, Sekiguchi, Mitsuaki, Somjing, Roongjang, Imanishi, Takeshi
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 18.03.2005; WILEY‐VCH Verlag; Wiley
• Subjects: Amides - chemistry; Base Sequence; Binding Sites; Chemistry; Chemistry, Multidisciplinary; conformation analysis; Hydrolysis; Ligands; Models, Chemical; Nucleic Acid Conformation; nucleic acids; Nucleic Acids - chemical synthesis; nucleosides; oligonucleotides; Oligonucleotides - chemistry; phosphoramidates; Phosphoric Acids - chemistry; Physical Sciences; Science & Technology; Temperature; Thymine - analogs & derivatives; Thymine - chemical synthesis; Time Factors; conformation analysis; CONSTRAINT CONFORMATIONAL FLEXIBILITY; TRICYCLO-DNA; nucleosides; NUCLEIC-ACID ANALOGS; nucleic acids; oligonucleotides; phosphoramidates

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.