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Oligonucleotide Analogues with Integrated Bases and Backbone. Part 20 : Hydrazide- and Amide-Linked Analogues. 1. Design and Synthesis of Monomeric Building Blocks

✍ Scribed by Manuel Peifer; Fabio De Giacomo; Martin Schandl; Andrea Vasella

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
740 KB
Volume
92
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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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).

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