Difficult macrocyclizations: New strategies for synthesizing highly strained cyclic tetrapeptides


Autoria(s): Meutermans, W.; Bourne, G. T.; Golding, S.; Horton, D.; Campitelli, M. R.; Craik, D. J.; Scanlon, M. J.; Smythe, M. L.
Contribuinte(s)

Amos B. Smith III

Data(s)

01/01/2003

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

http://espace.library.uq.edu.au/view/UQ:66449

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