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https://hdl.handle.net/2440/34467
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Type: | Journal article |
Title: | Synthesis and evaluation of eight-membered cyclic pseudo-dipeptides |
Author: | Abell, A. Brown, K. Coxon, J. Jones, M. Miyamoto, S. Neffe, A. Nikkel, J. Stuart, B. |
Citation: | Peptides, 2005; 26(2):251-258 |
Publisher: | Elsevier Science Inc |
Issue Date: | 2005 |
ISSN: | 0196-9781 1873-5169 |
Statement of Responsibility: | Andrew D. Abell, Karina M. Brown, James M. Coxon, Matthew A. Jones, Sigeru Miyamoto, Axel T. Neffe, Janna M. Nikkel and Blair G. Stuart |
Abstract: | 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. |
Keywords: | Peptidomimetics Molecular modeling Metathesis Cataract Calpain |
DOI: | 10.1016/j.peptides.2004.09.006 |
Description (link): | http://www.elsevier.com/wps/find/journaldescription.cws_home/525495/description#description |
Published version: | http://dx.doi.org/10.1016/j.peptides.2004.09.006 |
Appears in Collections: | Aurora harvest 6 Chemistry publications |
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