Synthesis and evaluation of eight-membered cyclic pseudo-dipeptides

In the course of the development of calpain inhibitors, we report the synthesis of eight-membered cyclic pseudo dipeptides closely related to the known inhibitor SJA6017. The ring closure was effected by metathesis of the diallyl-substituted dipeptides 6 and 7. The formation of the dipeptides under...

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Bibliographic Details
Published in:Peptides (New York, N.Y. : 1980) N.Y. : 1980), 2005-02, Vol.26 (2), p.251-258
Main Authors: Abell, Andrew D., Brown, Karina M., Coxon, James M., Jones, Matthew A., Miyamoto, Sigeru, Neffe, Axel T., Nikkel, Janna M., Stuart, Blair G.
Format: Article
Language:English
Subjects:
Biological and medical sciences
Calpain
Calpain - antagonists & inhibitors
Cataract
Computational Biology
Dipeptides - chemical synthesis
Dipeptides - chemistry
Fundamental and applied biological sciences. Psychology
Lens diseases
Medical sciences
Metathesis
Models, Molecular
Molecular modeling
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Ophthalmology
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Peptidomimetics
Protein Conformation
Vertebrates: endocrinology
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Summary:In the course of the development of calpain inhibitors, we report the synthesis of eight-membered cyclic pseudo dipeptides closely related to the known inhibitor SJA6017. The ring closure was effected by metathesis of the diallyl-substituted dipeptides 6 and 7. The formation of the dipeptides under kinetic control leads to the preferential formation of the unlike diastereomer 7 over the like diastereomer 6. The relative configuration of the diastereomers was determined by NMR and modeling studies of the related cyclic compounds 8 and 9 and their derivatives. The compounds proved not to inhibit calpain.
ISSN:0196-9781
1873-5169
DOI:10.1016/j.peptides.2004.09.006