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Synthesis and Properties of Oligodeoxynucleotides Possessing N ‐Phosphoryl Groups
Author(s) -
Moriguchi Tomohisa,
Wada Takeshi,
Sekine Mitsuo
Publication year - 2003
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/ejoc.200200294
Subject(s) - chemistry , steric effects , cytosine , stereochemistry , dna , oligonucleotide , phosphorylation , base pair , biochemistry
This paper deals with the synthesis and properties of oligodeoxynucleotides of a Dickerson−Drew sequence, d(CGCGAATTCGCG), in which one of the four cytosine bases has been replaced with an N ‐phosphorylated or N ‐diethylphosphorylated cytosine base in order to study the effect of the N ‐phosphoryl or N ‐diethoxyphosphoryl group on their structural property and hybridization affinity. The CD spectra of these self‐complementary duplexes showed the typical B DNA‐type shape with very minor changes. In contrast, it was found from T m experiments that N ‐phosphoryl groups destabilized the DNA duplexes significantly through steric hindrance and electronic repulsion. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)