Molecular recognition of N-acetyltryptophan enantiomers by β-cyclodextrin
The enantioselectivity of β-cyclodextrin (β-CD) towards L- and D-N-acetyltryptophan (NAcTrp) has been studied in aqueous solution and the crystalline state. NMR studies in solution show that β-CD forms complexes of very similar but not identical geometry with both L- and D-NAcTrp and exhibits stronger binding with L-NAcTrp. In the crystalline state, only β-CD–L-NAcTrp crystallizes readily from aqueous solutions as a dimeric complex (two hosts enclosing two guest molecules). In contrast, crystals of the complex β-CD–D-NAcTrp were never obtained, although numerous conditions were tried. In aqueous solution, the orientation of the guest in both complexes is different than in the β-CD–L-NAcTrp …
CCDC 1531987: Experimental Crystal Structure Determination
Related Article: Spyros D. Chatziefthimiou, Mario Inclán, Petros Giastas, Athanasios Papakyriakou, Konstantina Yannakopoulou and Irene M. Mavridis|2017|Beilstein J.Org.Chem.|13|1572|doi:10.3762/bjoc.13.157
CCDC 1531988: Experimental Crystal Structure Determination
Related Article: Spyros D. Chatziefthimiou, Mario Inclán, Petros Giastas, Athanasios Papakyriakou, Konstantina Yannakopoulou and Irene M. Mavridis|2017|Beilstein J.Org.Chem.|13|1572|doi:10.3762/bjoc.13.157