Premium
Conformational Analysis of the Cyclic Pentadepsipeptide Cyclo(Tro‐Aib‐Aib‐Aib‐Aib) in the Solid State and in Solution
Author(s) -
Koch Kristian N.,
Hopp Gudrun,
Linden Anthony,
Moehle Kerstin,
Heimgartner Heinz
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010228)84:2<502::aid-hlca502>3.0.co;2-#
Subject(s) - chemistry , solid state
The cyclic 16‐membered pentadepsipeptide cyclo(Tro‐Aib‐Aib‐Aib‐Aib) ( 1 ) was crystallized from MeOH/AcOEt/CH 2 Cl 2 , and its structure was established by X‐ray crystallography ( Fig. 1 ). There are two symmetry‐independent molecules with different conformations in the asymmetric unit. Two intramolecular H‐bonds stabilize two β ‐turns in each molecule. On the other hand, two of the four Aib residues are forced to assume a nonfavorable nonhelical conformation in each of the symmetry‐independent molecules ( Table 1 ). The conformational study in CDCl 3 solution by NMR spectroscopy and molecular dynamics (MD) simulations indicate that the averaged structure ( Fig. 3 ) is almost the same as in the solid state.