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Oligonucleotide Analogues with Integrated Bases and Backbone. Part 20
Author(s) -
Peifer Manuel,
De Giacomo Fabio,
Schandl Martin,
Vasella Andrea
Publication year - 2009
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.200900047
Subject(s) - chemistry , hydrazide , uracil , cytosine , curtius rearrangement , amide , nucleobase , acylation , oligonucleotide , hydrazine (antidepressant) , thymine , guanine , aniline , nucleophilic substitution , combinatorial chemistry , organic chemistry , dna , nucleotide , biochemistry , chromatography , gene , catalysis
Hydrazide‐ and amide‐linked oligonucleoside analogues with integrated bases and backbone were designed to allow for a rapid synthesis of long and water‐soluble oligomers. The uracil‐, cytosine‐, and adenine‐derived hydrazide building blocks 13 – 15 were synthesized by nucleophilic substitution with the hydrazine 23 of the halides 19, 28 , and 34 , derived from the alcohols 18, 27 , and 33 , respectively, while the uracil‐, cytosine‐, and adenine‐derived amide building blocks 45 – 47 were synthesized by a Curtius degradation of the carboxylic acids 51, 56 , and 61 . These acids were obtained by Wittig reaction of the aldehydes 49, 53 , and 58 . The guanine‐derived monomers 44 and 48 were synthesized by reductive cyclisation of the nitroso amides 38 and 63 , respectively, resulting from acylation of the known 2,6‐diamino‐4‐(benzyloxy)‐5‐nitrosopyrimidine ( 37 ).