Synthesis and Diversification of Pyridone Dipeptide Chromophores

Autor:	Harald Seger, Armin Geyer
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Dipeptide Bicyclic molecule Chemistry Stereochemistry Organic Chemistry Chemical biology Halogenation Regioselectivity Peptide Catalysis Coupling reaction chemistry.chemical_compound Lactam
Zdroj:	Synthesis. 2006:3224-3230
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2006-942546
Popis:	An improved synthetic protocol transforms D-alduronolactone via a bicyclic dipeptide lactam 2 into pyridone dipeptides with either Boc- or Fmoc-protecting groups 5 or 6. Regioselective bromination of 5 yields dipeptide 10 which is further diversified in Pd-catalyzed cross coupling reactions. This late diversification of a common peptide precursor makes a maximum number of rigid dipeptide chromophores accessible. The dipeptides 11, 12, and 13 exemplify a general strategy of accessing conformationally locked peptide chromophores as tools for chemical biology.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e09b47a7925000cbce0e0ee785434f25 https://doi.org/10.1055/s-2006-942546 Zobrazit plný text záznamu