Organic and Biomolecular Chemistry p. 3892 - 3893 (2006)
Update date:2022-08-03
Topics:
Marson, Charles M.
Saadi, Mona
The synthesis of the penta-oxazole core of telomestatin whose methyl derivative could be an advanced intermediate in its total synthesis by subsequent condensation with a suitably substituted oxazole was investigated. The biosynthesis of telomestatin was interpreted as a formal assembly of one cysteine, five serine, and two threonine sub-units. The successive use of amines bearing unprotected hydroxymethyl groups permitted iterative assembly of polyoxazoles without the need for repeated protection and deprotection. It also permitted regioselective introduction of substituents at the 5-position of one or more oxazole rings and a variety of analogues to probe telomerase function. The synthetic route also provided several linked polyoxazole systems of increasing complexity and derived from serine as the only amino acid.
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