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Synthesis of 2′‐Deoxyisoinosine and Related 2′‐Deoxyribonucleosides
Author(s) -
Seela Frank,
Chen Yaoming,
Bindig Uwe,
Kazimierczuk Zygmunt
Publication year - 1994
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.19940770122
Subject(s) - deoxyribonucleosides , chemistry , pyrimidine , nucleobase , deoxyguanosine , purine , glycosylation , stereochemistry , derivative (finance) , stereoselectivity , fluorescence , deoxyribonucleoside , dna , combinatorial chemistry , organic chemistry , biochemistry , catalysis , financial economics , economics , enzyme , physics , quantum mechanics
Various 2‐substituted purine and pyrrolo[2,3‐ d ]pyrimidine 2′‐deoxyribonucleosides with methylthio ( 13a ), chloro ( 13b ), methoxy ( 9b ), and oxo ( 2, 3 ) substituents at C(2) are prepared. They are obtained either via stereoselective nucleobase‐anion glycosylation or by base transformation. A three‐step synthesis of the unknown 2′‐deoxyisoinosine ( 2 ) from 2′‐deoxyguanosine ( 15 ) is described. Compound 2 as well as its 7‐deazapurine derivative 3 exhibit strong fluorescence.