Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 11, Pages 5507-5516Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00396
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Funding
- MIUR (PRIN) [Proj. 2010NRREPL]
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A new alpha,alpha-disubstituted constrained glutamine analogue has been designed to decorate gold nanopartides and to induce a 3(10)-helix when inserted in peptides. Using an efficient one-pot asymmetric Schmidt reaction between 4-disubstituted-cydohexanone and hydroxyalkylazides, 1H-azepine-2-oxo-5-amino-5-carboxylic acid was prepared. The main (R) isomer was inserted at the N-terminus in a very short peptide sequence (i.e., PhCO-(R)-Oxo-Azn-L-Ala-Aib-L-AlaNHMe) and a stable 3(10)-helix conformation was obtained, as verified by both NMR experiments and molecular dynamics (MD) simulations. Finally, the presence of the hydroxyl chain at the nitrogen atom of the ring allowed for the preparation of covered chiral gold nanopartides.
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