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Direct Structural Comparison of a Rigid Cyclic Peptidic Scaffold Using Crystallography and NMR in Strained PH Polymer Gels
Author(s) -
Arnusch Christopher J.,
Ippel Johannes H.,
Kooijman Huub,
Spek Anthony L.,
Liskamp Rob M. J.,
Kemmink Johan,
Pieters Roland J.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000440
Subject(s) - chemistry , polymer , molecule , crystal structure , ether , residual dipolar coupling , nuclear magnetic resonance spectroscopy , crystallography , stereochemistry , organic chemistry
A small series of biaryl ether containing cyclic peptidic scaffolds was synthesized and cyclized by an S N Ar reaction. The structure of one rigid scaffold was solved by X‐ray crystallography and also determined in solution by NMR spectroscopy. Molecular alignment of the peptidic scaffold in strained PH polymer gels in [D 6 ]DMSO was applied to extract residual dipolar couplings (RDCs). The RDC values were used to obtain a structure that was compared to the crystal structure. Good correlation was obtained, indicating that the RDC method represents a very precise structure determination method for small organic molecules in solution.