Premium
The Donor‐Acceptor‐Acceptor Purine Analog: Transformation of 5‐aza‐7‐deaza‐1 H ‐isoguanine (=4‐aminoimidazo‐[1,2‐ a ]‐1,3,5‐triazin‐2(1 H )‐one) to 2′‐deoxy‐5‐aza‐7‐deaza‐isoguanosine using purine nucleoside phosphorylase
Author(s) -
Voegel Johannes J.,
Altorfer Michael M.,
Benner Steven A.
Publication year - 1993
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.19930760520
Subject(s) - chemistry , purine nucleoside phosphorylase , yield (engineering) , acceptor , stereochemistry , purine , pyrimidine , purine metabolism , deoxyribonucleoside , derivative (finance) , oligonucleotide , anomer , combinatorial chemistry , enzyme , biochemistry , dna , materials science , physics , economics , financial economics , metallurgy , condensed matter physics
Abstract A new synthesis is reported for 4‐aminoimidazo[1,2‐ a ]‐1,3,5‐triazin‐2(1 H )‐one ( =5‐aza‐7‐deaza‐isoguanosine; 8 ), a purine analog that, when incorporated into an oligonucleotide chain, presents a H‐bond donor‐acceptor‐acceptor pattern to a complementary pyrimidine analog. A protected ribose derivative was coupled to 8 to yield 4‐amino‐8‐(β‐ D ‐ribofuranosyl)imidazo[1,2‐ a ]‐1,3,5‐triazin‐2(8 H )‐one ( =5‐aza‐7‐deaza‐isoguanosine; 11 ) after deprotection, Alternatively, direct synthesis of both the ribo derivative 11 and the corresponding deoxyribo derivative 17 as the β‐ D ‐anomers was achieved using the enzyme purine nucleoside phosphorylase in a one‐pot reaction. This adapts a known synthetic approach to yield a new strategy for obtaining diastereoisomerically pure deoxyribonucleoside analogs on 1‐gram scales.