Difficult macrocyclizations: New strategies for synthesizing highly strained cyclic tetrapeptides
Contribuinte(s) |
Amos B. Smith III |
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Data(s) |
01/01/2003
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Resumo |
Cyclic tetrapeptides are an intriguing class of natural products. To synthesize highly strained cyclic tetrapeptides; we developed a macrocyclization strategy that involves the inclusion of 2-hydroxy-6-nitrobenzyl (HnB) group at the N-terminus and in the middle of the sequence. The N-terminal auxiliary performs a ring closure/ring contraction role, and the backbone auxiliary promotes cis amide bonds to facilitate the otherwise difficult ring contraction. Following this route, the all-L cyclic tetrapeptide cyclo-[Tyr-Arg-Phe-Ala] was successfully prepared. |
Identificador | |
Idioma(s) |
eng |
Publicador |
American Chemical Society |
Palavras-Chave | #Chemistry, Organic #Natural-products #Combinatorial Synthesis #Conformational-analysis #Privileged Structures #Histone Deacetylase #Nmr Spectrometry #Drug Discovery #Peptides #Chlamydocin #Cyclization #C1 #250302 Biological and Medical Chemistry #780103 Chemical sciences |
Tipo |
Journal Article |