Premium
Oligonucleotide Analogues with a Nucleobase‐Including Backbone:, Part 6, 2‐Deoxy‐ D ‐erythrose‐Derived Phosphoramidites: Synthesis and Incorporation into 14‐Mer DNA Strands
Author(s) -
Czechtizky Werngard,
Vasella Andrea
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010516)84:5<1000::aid-hlca1000>3.0.co;2-s
Subject(s) - chemistry , nucleobase , stereochemistry , oligonucleotide , nucleotide , deoxyribose , uracil , nucleoside , dna , nucleic acid , duplex (building) , ribose , biochemistry , enzyme , gene
Two modified DNA 14‐mers have been prepared, containing either a 2‐deoxy‐ D ‐erythrose‐derived adenosine analogue carrying a C(8)−CH 2 O group (deA*), or a 2‐deoxy‐ D ‐erythrose‐derived uridine analogue, possessing a C(6)−CH 2 O group (deU*). These nucleosides are linked via a phosphinato group between O−C(3′) (deA* and deU*) and O−C(5′) of one neighbouring nucleotide, and between C(8)−CH 2 O (deA*), or C(6)−CH 2 O (deU*) and O−C(3′) of the second neighbour. N 6 ‐Benzoyl‐9‐( β ‐ D ‐erythrofuranosyl)adenine ( 3 ) and 1‐( β ‐ D ‐erythrofuranosyl)uracil ( 4 ) were prepared from D ‐glucose, deoxygenated at C(2′), and converted into the required phosphoramidites 1 and 2 . The modified tetradecamers 31 and 32 were prepared by solid‐phase synthesis. Pairing studies show a decrease in the melting temperature of 7 to 8 degrees for the duplexes 31 ⋅ 30 and 32 ⋅ 29 , as compared to the unmodified DNA duplex 29 ⋅ 30 . A comparison with the pairing properties of tetradecamers similarly incorporating deoxyribose‐ instead of the deoxyerythrose‐derived nucleotides evidences that the CH 2 OH substituent at C(4′) has no significant effect on the pairing.