Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification.
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.
Horton
Douglas A
DA
Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Qld 4072, Australia.
Bourne
Gregory T
GT
Coughlan
Justin
J
Kaiser
Sonya M
SM
Jacobs
Carolyn M
CM
Jones
Alun
A
Rühmann
Andreas
A
Turner
Jill Y
JY
Smythe
Mark L
ML
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
D010456:Peptides, Cyclic; D054852:Small Molecule Libraries