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

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.

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 44; no. 13; pp. 1944 - 1947
Main Authors Obika, Satoshi, Sekiguchi, Mitsuaki, Somjing, Roongjang, Imanishi, Takeshi
Format Journal Article
LanguageEnglish
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
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Summary: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.
Bibliography:istex:D17EADFE8A8D58CDE3BD69F784DA5FD346422FA8
ark:/67375/WNG-89CSD4SX-K
This research was partially supported by a Grant-in-Aid from the Japan Society for the Promotion of Science, a Grant-in-Aid from the Ministry of Education, Culture, Sports, Science, and Technology of Japan, and a SUNBOR Grant from the Suntory Institute for Bioorganic Research. We gratefully acknowledge a JSPS Research Fellowship for Young Scientists (M.S.).
ArticleID:ANIE200461942
This research was partially supported by a Grant‐in‐Aid from the Japan Society for the Promotion of Science, a Grant‐in‐Aid from the Ministry of Education, Culture, Sports, Science, and Technology of Japan, and a SUNBOR Grant from the Suntory Institute for Bioorganic Research. We gratefully acknowledge a JSPS Research Fellowship for Young Scientists (M.S.).
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200461942