Open AccessTotal synthesis of a xylo-Puromycin analog
Author(s) -
Benoît Y. Michel,
K. S. Krishnakumar,
Peter Strazewski
Publication year - 2008
Publication title -
nucleic acids symposium series
Language(s) - English
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/nrn291
Subject(s) - puromycin , acetylation , epoxide , chemistry , stereochemistry , adenosine , ring (chemistry) , organic chemistry , biochemistry , catalysis , protein biosynthesis , gene
N(6)-bis-demethylated xylo-Puromycin analog 2 was synthesized in 56% over 6 steps from adenosine 3, involving a Mattocks bromo acetylation, a regio- and stereo-selective ribo-epoxide ring opening with sodium azide and an efficient Staudinger-Vilarrasa coupling reaction for which the conditions have been optimized.
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