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. 1991 Feb 25;19(4):733-8.
doi: 10.1093/nar/19.4.733.

New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly

B S Sproat  1 , A M Iribarren, R G Garcia, B Beijer
Affiliations
Free PMC article

New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly

B S Sproat et al. Nucleic Acids Res. .
Free PMC article

Abstract

New synthetic routes have been devised for the high yield preparation of protected 2'-O-allylribonucleoside-3'-O-phosphoramidites, exemplified by the ribonucleosides guanosine and 2,6-diaminopurine riboside (2-aminoadenosine). Key features are the use of versatile intermediates and an easy allylation step. The development of a novel synthon based on 2'-O-allyl-2,6-diaminopurine riboside enables short 2'-O-allyl-oligoribonucleotide probes to be synthesized with adenine replaced by 2-aminoadenine. Thus very stable hybrids with complementary RNA target sequences can be formed due to the formation of the three hydrogen bond 2-amino A.U base pairs.

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