title: Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification.
abstract: Cyclic tetrapeptides are a class of natural products that have been shown to have broad ranging biological activities and good pharmacokinetic properties. In order to synthesise these highly strained compounds a ring contraction strategy had previously been reported. This strategy was further optimised and a suite of techniques, including the Edman degradation and mass spectrometry/mass spectrometry, were developed to enable characterisation of cyclic tetrapeptide isomers. An NMR solution structure of a cyclic tetrapeptide was also generated. To illustrate the success of this strategy a library of cyclic tetrapeptides was synthesised.
authors.affiliation: Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Qld 4072, Australia.
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Horton
authors.forename: Gregory T
authors.initials: GT
authors.lastname: Bourne
authors.forename: Justin
authors.initials: J
authors.lastname: Coughlan
authors.forename: Sonya M
authors.initials: SM
authors.lastname: Kaiser
authors.forename: Carolyn M
authors.initials: CM
authors.lastname: Jacobs
authors.forename: Alun
authors.initials: A
authors.lastname: Jones
authors.forename: Andreas
authors.initials: A
authors.lastname: Rühmann
authors.forename: Jill Y
authors.initials: JY
authors.lastname: Turner
authors.forename: Mark L
authors.initials: ML
authors.lastname: Smythe
mesh_terms: D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D012015:Reference Standards; D054852:Small Molecule Libraries; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry / Q000379:methods
chemical_list: D010456:Peptides, Cyclic; D054852:Small Molecule Libraries