Organic reactions in frozen water: Michael addition of amines and thiols to the dehydroalanine side chain of nocathiacins

Autor:	Wenying Li, Timothy P. Connolly, Yasutsugu Ueda, Oak K. Kim, B. Narasimhulu Naidu, John D. Matiskella, Kin Sing Lam, John A. Wichtowski, Joanne J. Bronson, Yunhui Zhang, Margaret E. Sorenson
Rok vydání:	2004
Předmět:	Chemistry Organic Chemistry Biochemistry Adduct chemistry.chemical_compound Organic reaction Nucleophile Dehydroalanine Drug Discovery Michael reaction Side chain Moiety Organic chemistry Amine gas treating
Zdroj:	Tetrahedron Letters. 45:1059-1063
ISSN:	0040-4039
Popis:	Nocathiacins are densely functionalized cyclic thiazolyl peptide natural products with potent in vitro and in vivo antibacterial activity against a variety of gram-positive bacteria, including a number of multiple drug-resistant strains. Attempts to prepare Michael adducts using known conditions resulted in the formation of complex mixture of products. In order to overcome this problem, we developed unique conditions in which Michael addition of amine and thiol nucleophiles to the dehydroalanine moiety of nocathiacins was successfully achieved in frozen water. Under these conditions, the Michael addition was highly chemoselective, very efficient and provided good isolated yields of the desired products.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a123e6127ee04ca876f6d958f6cb61a7 https://doi.org/10.1016/j.tetlet.2003.11.081 Zobrazit plný text záznamu Full Text from ScienceDirect