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Synthesis of Phosphonates and Oligodeoxyribonucleotides Derived from 2′-Deoxyisoguanosine and 2′-Deoxy-2-haloadenosines

✍ Scribed by Frank Seela; Ralf Mertens; Zygmunt Kazimierczuk

Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
512 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Oligonucleotides containing 2′‐deoxyisoguanosine (1) or 2‐chloro‐2′‐deoxyadenosine (2a) have been prepared by solid‐phase synthesis. Suitably protected phosphonates 3a, 4a, and 4b as well as the phosphoramidite of 1 have been obtained from the nucleosides 1, 2a, or 2b via the (dimethylamino)methylidene derivatives 5–7. 4,4′‐Dimethoxytrityl groups were introduced to yield the base‐protected derivatives 8–10. Alternatively to the direct incorporation of 1 into oligonucleotides, they were also obtained by the photochemical conversion of a 2a residue within the oligonucleotide chain.

📜 SIMILAR VOLUMES

Facile Synthesis of 2′-Deoxyisoguanosine
Facile Synthesis of 2′-Deoxyisoguanosine and Related 2′,3′-Dideoxyribonucleosides
✍ Frank Seela; Bert Gabler 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 German ⚖ 519 KB

## Abstract The 2′‐deoxyisoguanosine (1) was synthesized by a two‐step procedure from 2′‐deoxyguanosine (5). Amination of silylated 2′‐deoxyguanosine yielded 2‐amino‐2′‐deoxyadenosine (6) which was subjected to selective deamination of the 2‐NH~2~ group resulting in compound 1. Also 2′,3′‐dideoxyis