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Syntheses of [1‐ 15 N]‐2′‐Deoxyinosine, [4‐ 15 N]‐2′‐DeoxyAICAR, and [1‐ 15 N]‐2′‐Deoxyguanosine
Author(s) -
Catalanotti Bruno,
De Napoli Lorenzo,
Galeone Aldo,
Mayol Luciano,
Oliviero Giorgia,
Piccialli Gennaro,
Varra Michela
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2235::aid-ejoc2235>3.0.co;2-x
Subject(s) - chemistry , deoxyguanosine , stereochemistry , organic chemistry , adduct
A high‐yield synthesis of [1‐ 15 N]‐2′‐deoxyinosine ( 5 ), [4‐ 15 N]‐2′‐deoxyAICAR ( 7 ), and [1‐ 15 N]‐2′‐deoxyguanosine ( 10 ) from 2′‐deoxyinosine ( 1 ) using relatively low expensive 15 NH 3 as 15 N source is described. The method exploits 2‐C reactivity of 2′‐deoxyinosine ( 1 ) to obtain its 15 N‐labelled counterpart, through [1‐ 15 N]‐2′‐deoxyinosine ( 5 ), and successively, [4‐ 15 N]‐2′‐deoxyAICAR ( 7 ). [1‐ 15 N]‐2′‐Deoxyguanosine ( 10 ) can be prepared as well, through an improved cyclization procedure. No protection of sugar hydroxyl groups is required at any stage.