Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/94288
Title: Model for the Reduced Schiff Base Intermediate between Amino Acids and Pyridoxal: Copper(II) Complexes of N-(2-Hydroxybenzyl)amino Acids with Nonpolar Side Chains and the Crystal Structures of [Cu(N-(2-hydroxybenzyl)-D,L-alanine)(phen)]·H2O and [Cu(N-(2-hydroxybenzyl)-D,L-alanine)(imidazole)]
Authors: Koh, L.L. 
Ranford, J.O. 
Robinson, W.T.
Svensson, J.O.
Tan, A.L.C. 
Wu, D.
Issue Date: 1996
Citation: Koh, L.L.,Ranford, J.O.,Robinson, W.T.,Svensson, J.O.,Tan, A.L.C.,Wu, D. (1996). Model for the Reduced Schiff Base Intermediate between Amino Acids and Pyridoxal: Copper(II) Complexes of N-(2-Hydroxybenzyl)amino Acids with Nonpolar Side Chains and the Crystal Structures of [Cu(N-(2-hydroxybenzyl)-D,L-alanine)(phen)]·H2O and [Cu(N-(2-hydroxybenzyl)-D,L-alanine)(imidazole)]. Inorganic Chemistry 35 (22) : 6466-6472. ScholarBank@NUS Repository.
Abstract: Copper(II) complexes with reduced Schiff base ligands of amino acids possessing nonpolar side chains with salicylaldehyde have been synthesized. Ternary complexes with imidazole, 1,10-phenanthroline, and pyridine have been prepared and characterized for N-(2-hydroxybenzyl)-D,L-alanine. The crystal structures of [(N-(2-hydroxybenzyl)-D,L-alanine)(1,10-phenanthroline)Cu(II)] monohydrate ([Cu(SAla)phen]·H2O) and [(N-(2-hydroxybenzyl)-D,L-alanine)(imidazole)Cu(II)] ([Cu(SAla)Him]), have been determined. [Cu(SAla)phen]·H2O crystallized in space group P1̄, with a = 8.718(2) Å, b = 10.886(3) Å, c = 11.693(2) Å, α = 71.32(2)°, β= 85.27(2)°, γ = 70.21(2)°, and Z = 2. The copper atom is five coordinate, with SAla acting as a tridentate ONO chelator through the carboxylato and phenolato oxygens and the amine nitrogen. The remaining donors are provided by the phen nitrogens. [Cu(SAla)Him] crystallized in space group P21/n, with a = 10.353(1) Å, b = 6.714(1) Å, c = 18.769(2) Å, β= 91.71(1)°, and Z = 4. The copper atom is four coordinate, with SAla acting as a tridentate ONO chelator with the neutral imidazole moiety coordinated through nitrogen. In both complexes the ligand has two chiral centers due to the coordination of the N. Molecular mechanics calculations show that unfavorable steric interactions would occur in the nonobserved R,R and S,S diastereomers. Compounds prepared have been characterized by a range of physicochemical techniques. The complexes may serve as stable models for the intermediates in enzymatic amino acid transformations.
Source Title: Inorganic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/94288
ISSN: 00201669
Appears in Collections:Staff Publications

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