Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 49, Pages 13600-13604Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406886
Keywords
amino acids; hydrogen bonds; polymorphism; pseudosymmetry; racemic twins
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Funding
- Department of Chemistry, University of Oslo
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The solid-state structure of the amino acid phenylalanine (Phe) offers a potential key to understanding the behavior of a large class of important aromatic compounds. Obtaining good single crystals is, however, notoriously difficult. The structure of the common polymorph of Phe, form I, was first reported by Weissbuch et al. (as D-Phe) in 1990, but the correctness of the published C2 unit cell with two disordered molecules in the asymmetric unit was later questioned and other space groups suggested. The identity of form I of L-Phe is here established to be P2(1) with Z ' = 4, based on data from a well-diffracting single crystal grown from an acetic acid solution of the amino acid. A second new polymorph, form IV, together with the two recently described forms II and III provide unprecedented information on the structural complexity of this essential amino acid. It is furthermore documented that the racemate, DL-Phe, does not grow proper single crystals.
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