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Synthesis of 3-(2-hydroxy-1-phenylethyl)- and 3-(2-hydroxy-2-phenylethyl)adenine, DNA adducts derived from styrene

✍ Scribed by Jan Krouželka; Igor Linhart; Tomáš Tobrman

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
319 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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3‐(2‐Hydroxy‐2‐phenylethyl)‐ and 3‐(2‐hydroxy‐1‐phenylethyl)adenine, DNA adducts derived from styrene, along with their 9‐substituted analogues were prepared by alkylation of 8‐bromoadenine with corresponding allyl‐protected bromohydrins followed by a new deallylation procedure using tetrakis(triphenylphosphine)palladium catalyzed reductive cleavage by poly(methylhydrosiloxane) in the presence of p‐toluenesulphonic acid. This novel procedure proved to be useful for purine derivatives, which were resistant to other deallylation protocols. Structure of positional isomers was assigned using 2D NMR experiments HMBC and HMQC.

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ChemInform Abstract: Synthesis of 3-(2-H
ChemInform Abstract: Synthesis of 3-(2-Hydroxy-1-phenylethyl)- and 3-(2-Hydroxy-2-phenylethyl)adenine, DNA Adducts Derived from Styrene.
✍ Jan Krouzelka; Igor Linhart; Tomas Tobrman 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

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Syntheses of 7-(2-Hydroxy-1-phenylethyl)
Syntheses of 7-(2-Hydroxy-1-phenylethyl)- and 7-(2-Hydroxy-2-phenylethyl)guanine, DNA Adducts Derived from Styrene 7,8-Oxide
✍ Jan Novák; Igor Linhart; Hana Dvorˇáková 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 English ⚖ 222 KB

## Abstract 7‐(2‐Hydroxy‐1‐phenylethyl)‐ and 7‐(2‐hydroxy‐2‐phenylethyl)guanines are important DNA adducts which can be used as markers of exposure to styrene. Two synthetic routes leading to these compounds are presented using allyl‐protected bromohydrins as synthetic equivalents of styrene oxide