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Essential Factors for Stabilization of the Predominant C3′‐ endo Conformation in Dinucleoside Phosphotriester Derivatives with Cyclonucleotide Bridge Structures at the Downstream 3′‐Position
Author(s) -
Sekine Mitsuo,
Kurasawa Osamu,
Shohda Kohichiroh,
Seio Kohji,
Wada Takeshi
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1989::aid-ejoc1989>3.0.co;2-h
Subject(s) - chemistry , stereochemistry , linker , nucleoside , diastereomer , residue (chemistry) , oligonucleotide , uracil , nucleotide , organic chemistry , biochemistry , dna , computer science , gene , operating system
This paper describes the synthesis of conformationally constrained dinucleoside cyclic phosphotriester derivatives and related compounds, such as Tpc3Um ( 2 ), Tpc3dU ( 3 ), Tpc2dU ( 4 ), pc3dU ( 16 ), and pc2dU ( 25 ), where c2 and c3 refer to ethylene and propylene bridges between the 5′‐phosphate of the 3′‐downstream nucleoside and the 5‐position of the uracil residue. These studies found that the c3 linker is essential for fixing the 3′‐downstream nucleoside residue in the C3′‐ endo puckering. The presence of the 2′‐hydroxyl group at the 3′‐downstream nucleoside is also crucial for stabilization of the C3′‐ endo conformation. Two sets of diastereomeric oligonucleotides, T 4 (Tpc3Um)T 4 ( 30 ) and T 4 (Tpc3dU)T 4 ( 33 ), were synthesized, and each stereoisomer was isolated. The hybridization capability of these oligonucleotides was analyzed by melting point experiments.