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Crystal structure of (4 S )‐aminoproline: conformational insight into a pH‐responsive proline derivative
Author(s) -
Siebler Christiane,
Trapp Nils,
Wennemers Helma
Publication year - 2015
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2734
Subject(s) - chemistry , derivative (finance) , conformational isomerism , trifluoroacetic acid , crystal structure , proline , aqueous solution , stereochemistry , peptide bond , ring (chemistry) , amide , trifluoroacetic anhydride , peptide , crystallography , amino acid , molecule , medicinal chemistry , organic chemistry , biochemistry , financial economics , economics
The crystal structure of a (4 S )‐configured ammoniumproline derivative is presented. The trifluoroacetic acid salt of the acetylated methylester of (4 S )‐aminoproline (Ac‐(4 S )Amp‐OMe) crystallized as the trans conformer with a C(4)‐ endo ring pucker. The high‐resolution structure shows typical parameters for a transannular H‐bond and an n → π* interaction between the adjacent amide and ester groups. The structure corroborates previous findings of solution phase studies on the importance of these two interactions in acidic and neutral aqueous environments for the conformation of this pH‐responsive proline derivative. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.