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Nucleotides. Part XLVII. Synthesis of 3′‐Deoxyadenylyl‐(2′–5′)‐3′‐deoxyadenylyl‐(2′–5′)‐3′‐ O ‐(2‐hydroxyethyl)adenosine and 3′‐Deoxyadenylyl‐(2′–5′)‐3′‐deoxyadenylyl‐(2′–5′)‐3′‐ O ‐{2‐[(cholest‐5‐en‐3β‐yloxy)carbonyloxy]ethyl}adenosine: A New Type of (2′–5′)Adenylate Trimer Conjugate
Author(s) -
Hörndler Cornelia,
Pfleiderer Wolfgang
Publication year - 1996
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.19960790314
Subject(s) - chemistry , phosphoramidite , moiety , cordycepin , trimer , stereochemistry , deoxyadenosine , adenosine , dimer , derivative (finance) , organic chemistry , oligonucleotide , biochemistry , dna , financial economics , economics
A suitably protected adenosine derivative bearing an acetyl‐protected 2‐hydroxyethyl moiety in 3′‐ O ‐position was attached to the 2′‐terminus of a cordycepin (3′‐deoxyadenosine) dimer. Coupling was performed by phosphoramidite chemistry using two alternative approaches – condensation of 5′‐phosphoramidite 16 with 2′‐OH cordycepin dimer 18 and condensation of dimeric cordycepin phosphoramidite 19 with 5′‐OH adenosine derivative 15 – of which the latter synthesis worked best (→ 20 ). After cleavage of the acetyl protecting group (→ 21 ), cholesteryl carbonate was introduced into the OH function of the spacer (→ 24 ). Final deblocking of trimer 24 with, or trimer 21 without the cholesterol moiety afforded the modified cordycepin conjugates 25 and 23 , respectively.