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Org Lett. 2007 Jul 19;9(15):2787-90. Epub 2007 Jun 26.

Facile and rapid access to inosine puromycin analogues through the use of adenylate deaminase.

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1
Laboratoire de Synthèse de Biomolécules, UMR 5246, ICBMS, Bâtiment Eugène Chevreul 5ième Etage, Université Claude Bernard Lyon 1, Villeurbanne Cedex, France.

Abstract

To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.

PMID:
17592852
DOI:
10.1021/ol070818q
[Indexed for MEDLINE]
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