Journal
ISRAEL JOURNAL OF CHEMISTRY
Volume 57, Issue 3-4, Pages 292-302Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ijch.201600106
Keywords
methanoproline; diketopiperazine; amide isomerization; natural bond orbital
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Funding
- Hoover Foundation Brussels Fellowship from the Belgian American Educational Foundation (BAEF)
- U.S. Department of State
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Herein we disclose a combined experimental and theoretical study on the conformational properties of amide bonds involving diastereomeric 4,5-methano-L-proline congeners as N-acetyl ethyl esters and dimeric amide ethyl esters as substrates for cyclization to diketopiperazines. The results are discussed in light of density functional theory calculations aimed at delineating the importance of the n* stabilization of the trans-amide conformations. The transitions states for the cyclization of diastereomeric 4,5-methano-L-proline ethyl esters to diketopiperazines were calculated and correlated to the experimental studies.
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