1I9P

CARBONIC ANHYDRASE II (F131V) COMPLEXED WITH 4-(AMINOSULFONYL)-N-[(2,4,6-TRIFLUOROPHENYL)METHYL]-BENZAMIDE

Summary for 1I9P

• Entry DOI: 10.2210/pdb1i9p/pdb
• Related: 1I9L 1I9M 1I9N 1I9O 1I9Q 1g1d 1g3z 1g45 1g46 1g48 1g4j 1g4o 1g52 1g53 1g54
• Descriptor: CARBONIC ANHYDRASE II, ZINC ION, MERCURY (II) ION, ... (5 entities in total)
• Functional Keywords: human carbonic anhydrase ii, 4-(aminosulfonyl)-n-[(2, 4, 6-trifluorophenyl)methyl]-benzamide, lyase
• Biological source: Homo sapiens (human)
• Cellular location: Cytoplasm : P00918
• Total number of polymer chains: 1
• Total formula weight: 29720.13

Authors

Kim, C.-Y.,Chandra, P.P.,Jain, A.,Christianson, D.W. (deposition date: 2001-03-20, release date: 2001-03-28, Last modification date: 2024-02-07)

Primary citation

Kim, C.Y.,Chandra, P.P.,Jain, A.,Christianson, D.W.
Fluoroaromatic-fluoroaromatic interactions between inhibitors bound in the crystal lattice of human carbonic anhydrase II.
J.Am.Chem.Soc., 123:9620-9627, 2001

PubMed Abstract: Intermolecular interactions of eleven different fluoroaromatic inhibitors are probed within the scaffolding of the crystal lattice of Phe-131-->Val carbonic anhydrase II. The degree and pattern of fluorine substitution on the inhibitor benzyl ring modulate its size, shape, and electronic character. In turn, these properties affect the geometry of intermolecular interactions between the fluoroaromatic rings of two different inhibitor molecules bound in the crystal lattice, as determined by X-ray crystallography. Depending on the degree and pattern of fluorine substitution, we observe a face-to-face (aromatic-aromatic) interaction, an atom-to-face (carbonyl-aromatic) interaction, or no interaction at all. These interaction geometries are analyzed with regard to van der Waals, electrostatic, and possible charge-transfer effects. For the aromatic-aromatic interactions investigated in this study, with aromatic ring quadrupoles specifically "tuned" by the degree and pattern of fluorination, the structural results suggest that London forces and charge-transfer complexation dominate over weakly polar electrostatic interactions in the association of aromatic ring pairs.

PubMed: 11572683
DOI: 10.1021/ja011034p

Experimental method

X-RAY DIFFRACTION (1.92 Å)