Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 21, Pages 8579-8582Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8013963
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Funding
- ANR (National Research Agency)
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The cyclization of aza-beta(3)-tetrapeptides gives access to new CTP (cyclotetrapeptide) analogues. These stereocontrolled templates are assembled without any asymmetric synthesis. X-ray crystallographic structure and NMR analysis show that the macrocyclic scaffold is characterized by a fully cooperative intramolecular H-bond network, in sharp contrast with the nanotubular assemblies observed for beta(3)-cyclotetrapeptides. This folding property reduces considerably the polarity of aza-beta(3)-tetrapeptides and should be useful in addressing intracellular targets.
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