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Synthesis and structural properties of Patellamide A derivatives and their Copper(ii) compounds

The synthesis, characterization and copper(II) coordination chemistry of three new cyclic peptide ligands, PatJ1 (cyclo-(Ile-Thr-(Gly)Thz-Ile-Thr-(Gly)Thz)), PatJ2 (cyclo-(Ile-Thr-(Gly)Thz-(D)-Ile-Thr-(Gly)Thz)), and PatL (cyclo-(Ile-Ser-(Gly)Thz-Ile-Ser-(Gly)Thz)) are reported. All of these cyclic...

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Bibliographic Details
Main Authors: Bernhardt, Paul V. (Author) , Comba, Peter (Author)
Format: Article (Journal)
Language:English
Published: 18 March 2002
In: Chemistry - a European journal
Year: 2002, Volume: 8, Issue: 7, Pages: 1527-1536
ISSN:1521-3765
DOI:10.1002/1521-3765(20020402)8:7<1527::AID-CHEM1527>3.0.CO;2-F
Online Access:Verlag, Pay-per-use, Volltext: http://dx.doi.org/10.1002/1521-3765(20020402)8:7<1527::AID-CHEM1527>3.0.CO;2-F
Verlag, Pay-per-use, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/1521-3765(20020402)8:7<1527::AID-CHEM1527>3.0.CO;2-F/abstract
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Author Notes:Paul V. Bernhardt, Peter Comba, David P. Fairlie, Lawrence R. Gahan, Graeme R. Hanson, and Lutz Lötzbeyer
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Summary:The synthesis, characterization and copper(II) coordination chemistry of three new cyclic peptide ligands, PatJ1 (cyclo-(Ile-Thr-(Gly)Thz-Ile-Thr-(Gly)Thz)), PatJ2 (cyclo-(Ile-Thr-(Gly)Thz-(D)-Ile-Thr-(Gly)Thz)), and PatL (cyclo-(Ile-Ser-(Gly)Thz-Ile-Ser-(Gly)Thz)) are reported. All of these cyclic peptides and PatN (cyclo-(Ile-Ser-(Gly)Thz-Ile-Thr-(Gly)Thz)) are derivatives of patellamide A and have a [24]azacrown-8 macrocyclic structure. All four synthetic cyclic peptides have two thiazole rings but, in contrast to patellamide A, no oxazoline rings. The molecular structure of PatJ1, determined by X-ray crystallography, has a saddle conformation with two close-to-coparallel thiazole rings, very similar to the geometry of patellamide D. The two coordination sites of PatJ1 with thiazole-N and amide-N donors are each well preorganized for transition metal ion binding. The coordination of copper(ii) was monitored by UV/Vis spectroscopy, and this reveals various (meta)stable mono- and dinuclear copper(ii) complexes whose stoichiometry was confirmed by mass spectra. Two types of dinuclear copper(ii) complexes, [Cu2(H4L)(OH2)n]2+ (n=6, 8) and [Cu2(H2L)(OH2)n] (n=4, 6; L=PatN, PatL, PatJ1, PatJ2) have been identified and analyzed structurally by EPR spectroscopy and a combination of spectra simulations and molecular mechanics calculations (MM-EPR). The four structures are similar to each other and have a saddle conformation, that is, derived from the crystal structure of PatJ1 by a twist of the two thiozole rings. The small but significant structural differences are characterized by the EPR simulations.
Item Description:Gesehen am 06.03.2018
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/1521-3765(20020402)8:7<1527::AID-CHEM1527>3.0.CO;2-F

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