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Functionalized Derivatives of Benzocrown Ethers, II. Supramolecular Complexes of L ‐Amino Acids as Efficient Activators of the Zinc Enzyme Carbonic Anhydrase
Author(s) -
Barboiu Mihai,
Supuran Claudiu T.,
Scozzafava Andrea,
Briganti Fabrizio,
Luca Constantin,
Popescu Georgeta,
Cot Louis,
Hovnanian Nadine
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970908
Subject(s) - chemistry , moiety , supramolecular chemistry , carbonic anhydrase , zinc , histidine , stereochemistry , amino acid , enzyme , carboxylate , ammonium , combinatorial chemistry , organic chemistry , biochemistry , molecule
The preparation of a series of supramolecular complexes of the ammonium salt of 2,3,11,12‐bis[4‐(10‐aminodecylcarbonyl)]benzo‐18‐crown‐6 with different natural and non‐natural amino acids is reported. In all these ditopic supramolecular complexes, with the exception of the histidine derivative, the ammonium moiety of the amino acid is anchored by means of hydrogen bonds within the macrocyclic cavity of the host, whilst the carboxylate moiety interacts with the ammonium group of the derivatized crown ether. The new complexes act as very efficient activators of the zinc enzyme carbonic anhydrase (isozymes I and II).