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Nucleotides. Part LVII. . Synthesis of phosphoramidite building blocks of 2′‐amino‐2′‐deoxyribonucleosides: New compounds for oligonucleotide synthesis
Author(s) -
Greiner Beate,
Pfleiderer Wolfgang
Publication year - 1998
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/hlca.19980810556
Subject(s) - chemistry , phosphoramidite , deoxyribonucleosides , oligonucleotide , cytosine , oligonucleotide synthesis , guanine , nucleoside , nucleotide , uracil , stereochemistry , solid phase synthesis , combinatorial chemistry , deoxyribonucleotide , organic chemistry , biochemistry , dna , peptide , gene
The chemical synthesis of 2′‐amino‐2′‐deoxyribonucleosides of uracil, cytosine, adenine, and guanine, and their conversion into suitably protected 3′‐phosphoramidite building blocks 35 – 40 for oligonucleotide synthesis are described. The aglycone and the 2′‐amino functions were protected using the 2‐(4‐nitrophenyl)ethoxycarbonyl (npeoc) group. The synthesis of the 3′‐ O ‐succinyl (3′‐ O ‐(3‐carboxypropanoyl))‐substituted starting nucleoside 41 is described and its behavior examined in solution and on solid phase with regard to an anticipated migration during 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) deprotection. Oligonucleotides were prepared using the new building blocks, and their hybridization properties were studied by UV‐melting techniques.