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

N. Malquin | Zendy; Keyvan Rahgoshay | Zendy; Nathalie Lensen | Zendy; Grégory Chaume | Zendy; Emeric Miclet | Zendy; Thierry Brigaud | Zendy

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

Author(s) -

N. Malquin,

Keyvan Rahgoshay,

Nathalie Lensen,

Grégory Chaume,

Emeric Miclet,

Thierry Brigaud

Publication year - 2019

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/c9cc05771d

Subject(s) - intramolecular force , hydrogen bond , chemistry , group (periodic table) , peptide bond , amide , hemiacetal , stereochemistry , molecular geometry , crystallography , peptide , molecule , organic chemistry , biochemistry

CF 2 H-Pseudoprolines obtained from difluoroacetaldehyde hemiacetal and serine are stable proline surrogates. The consequence of the incorporation of the CF 2 H 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.

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