CF2H as hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines - Archive ouverte HAL
Article Dans Une Revue Chemical Communications Année : 2019

CF2H as hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines

Résumé

CF2H-Pseudoprolines obtained from difluoroacetaldehyde hemiacetal and serine are stable proline surrogates. The consequence of the incorporation of the CF2H group is an important decrease of the trans to cis amide bond isomerization energy and a remarkable stabilisation of the cis conformer by an hydrogen bond.

Domaines

Chimie organique
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Dates et versions

hal-03549249 , version 1 (31-01-2022)

Identifiants

Citer

N Malquin, K Rahgoshay, N Lensen, G Chaume, E Miclet, et al.. CF2H as hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines. Chemical Communications, 2019, 55 (83), pp.12487-12490. ⟨10.1039/C9CC05771D⟩. ⟨hal-03549249⟩
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