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An expeditious route to methylphosphonate analogues of DNA

✍ Scribed by E. Kuyl-Yeheskiely; N. J. Meeuwenoord; G. A. van der Marel; J. H. van Boom

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
498 KB
Volume
113
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Protection of the exocyclic amino groups of both nucleobases adenine and guanine with the N,N‐dimethylformamidine and cytosine with the isobutyryl group presents a convenient and economical N‐protective‐group‐strategy for the solid‐phase synthesis of DNA fragments containing methylphosphonate linkages at predetermined locations. Thus, the post‐synthesis removal of the N‐protective groups with hydrazine hydrate (16 h at 20°C) afforded immobilized fragments, which were then cleaved from the solid support and deprotected at the phosphorus by treatment with ammonia in methanol (2 h at 20°C) to yield high‐quality products.

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