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Channel‐like crystal structure of cinchoninium L ‐ O ‐phosphoserine salt dihydrate
Author(s) -
WesełuchaBirczyńska Aleksandra,
Oleksyn Barbara J.,
Wątroba Joanna
Publication year - 2010
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20784
Subject(s) - chemistry , crystallography , hydrogen bond , molecule , monoclinic crystal system , cinchonine , crystal structure , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
Studies on the interactions between L ‐ O ‐ phosphoserine, as one of the simplest fragments of membrane components, and the Cinchona alkaloid cinchonine, in the crystalline state were performed. Cinchoninium L ‐ O ‐phosposerine salt dihydrate (PhSerCin) crystallizes in a monoclinic crystal system, space group P2 1 , with unit cell parameters: a = 8.45400(10) Å, b = 7.17100(10) Å, c = 20.7760(4) Å, α = 90°, β = 98.7830(10)°, γ = 90°, Z = 2. The asymmetric unit consists of the cinchoninium cation linked by hydrogen bonds to a phosphoserine anion and two water molecules. Intermolecular hydrogen bonds connecting phosphoserine anions via water molecules form chains extended along the b axis. Two such chains symmetrically related by twofold screw axis create a “channel.” On both sides of this channel cinchonine cations are attached by hydrogen bonds in which the atoms N1, O12, and water molecules participate. This arrangement mimics the system of bilayer biological membrane. Chirality 2010. © 2009 Wiley‐Liss, Inc.