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Effect of the Solvent on the Conformation of a Depsipeptide: NMR‐Derived Solution Structure of Hormaomycin in DMSO from Residual Dipolar Couplings in a Novel DMSO‐Compatible Alignment Medium
Author(s) -
Reinscheid Uwe M.,
Farjon Jonathan,
Radzom Markus,
Haberz Peter,
Zeeck Axel,
Blackledge Martin,
Griesinger Christian
Publication year - 2006
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200500277
Subject(s) - chemistry , moiety , residual dipolar coupling , depsipeptide , solvent , nuclear magnetic resonance spectroscopy , crystallography , stereochemistry , organic chemistry
The macrocyclic compound hormaomycin has been investigated by NMR spectroscopy and by restrained molecular‐dynamics simulations. Measurement of residual dipolar couplings induced by dissolving the depsipeptide in a polyacrylamide gel compatible with DMSO and their incorporation into the structure calculation of the title compound improved the precision of the family of structures. In DMSO the macrocyclic ring shows two β‐turns, whose positions in the sequence differ from those found in the CDCl 3 solution structure and in the crystal structure obtained from hexylene glycol/H 2 O (50:50). The bulky side chain consisting of a 3‐(2‐nitrocyclopropyl)alanine and a chlorinated N ‐hydroxypyrrole moiety is flexible in DMSO.