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Nucleotides. Part XXXI . Modified Oligomeric 2′–5′ A Analogues: Synthesis of 2′–5′ oligonucleotides with 9‐(3′‐azido‐3′‐deoxy‐β‐ D ‐xylofuranosyl)adenine and 9‐(3′‐amino‐3′‐deoxy‐β‐ D ‐xylofuranosyl)adenine as modified nucleosides
Author(s) -
Herdewijn Piet,
Charubala Ramamurthy,
Pfleiderer Wolfgang
Publication year - 1989
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.19890720810
Subject(s) - chemistry , trimer , moiety , oligonucleotide , stereochemistry , nucleotide , dimer , organic chemistry , biochemistry , dna , gene
A series of new 2′–5′ oligonucleotides carrying the 9‐(3′‐azido‐3′deoxy‐β‐D‐xylofuranosyl)adenine moiety as a building block has been synthesized via the phosphotriester method. The use of the 2‐(4‐nitrophenyl)ethyl (npe) and 2‐(4‐nitrophenyl)ethoxycarbonyl (npeoc) blocking groups for phosphate, amino, and hydroxy protection guaranteed straightforward syntheses in high yields and easy deblocking lo form the 2′–5′ trimers 21 , 22 , and 25 and the tetramer 23 . Catalytic reduction of the azido groups in [9‐(3′‐azido‐3′‐deoxy‐β‐D‐xylofuranosyl)adenine]2′‐yl‐[2′‐(O p ‐ammonio)→ 5′]‐[9‐(3′‐azido‐3′‐deoxy‐β‐D‐xylofuranosyl)adenin]‐2′‐yl‐[2′‐(O p ‐ammonio)→ 5′]‐9‐(3′‐azido‐3′‐deoxy‐β‐D‐xylofuranosyl)adenine ( 21 ) led to the corresponding 9‐(3′‐amino‐3′‐deoxy‐β‐D‐xylofuranosyl)‐adenine 2′–5′ trimer 26 in which the two internucleotidic linkages are formally neutralized by intramolecular betaine formation.