Metallamacrocycle formation through dimerization of metal bioconjugates derived from amino acids and peptides

被引:5
作者
Alvarez, Celedonio M. [1 ]
Garcia-Rodriguez, Raul [1 ]
Miguel, Daniel [1 ]
机构
[1] Univ Valladolid, Fac Ciencias, GIR MIOMET IU CINQUIMA Quim Inorgan, E-47005 Valladolid, Spain
关键词
DERIVATIZED DIIMINE LIGANDS; THIOLATE NUCLEOPHILICITY; CARBONYL-COMPLEXES; TUNGSTEN COMPOUNDS; CRYSTAL-STRUCTURE; HYDROGEN-BOND; MOLYBDENUM; RHENIUM; DESIGN; EPIMERIZATION;
D O I
10.1039/c5dt01256b
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Metallamacrocycles of 12, 16, and 22 members are obtained by deprotonation of the carboxylic group of the side chain of iminopyridine complexes derived from the amino acid beta-alanine, and the peptides Gly-Gly and Gly-Gly-Gly. Instead of the expected intramolecular attack to give tridentate (N, N, O) ligands, the deprotonated carboxylate attacks in an inter-molecular manner to give dimers in which the ligand acts as a bridge bonded in a kappa(2)(N, N') chelating fashion to one metal and as kappa(O) to the other metal. The formation of the dimers is supported by NMR spectroscopy, mass spectrometry and X-ray crystallography.
引用
收藏
页码:963 / 972
页数:10
相关论文
共 47 条
[1]   First application of fac-[99mTc(OH2)3(CO)3]+ in bioorganometallic chemistry:: Design, structure, and in vitro affinity of a 5-HT1A receptor ligand labeled with 99mTc [J].
Alberto, R ;
Schibli, R ;
Schubiger, AP ;
Abram, U ;
Pietzsch, HJ ;
Johannsen, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) :6076-6077
[2]   Metallacyclopeptides: Artificial analogues of naturally occurring peptides [J].
Albrecht, M ;
Stortz, P .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (06) :496-506
[3]   Preparation of tripeptide-bridged dicatechol Ligands and their macrocyclic molybdenum(VI) complexes: Fixation of the RGD sequence and the WKY sequence of urotensin II in a cyclic conformation [J].
Albrecht, M ;
Stortz, P ;
Runsink, J ;
Weis, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (15) :3657-3666
[4]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[5]   Carbonyl complexes of manganese, rhenium and molybdenum with 2-pyridylimino acid ligands [J].
Alvarez, Celedonio M. ;
Garcia-Rodriguez, Raul ;
Miguel, Daniel .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (26) :5717-5726
[6]   Pyridine-2-carboxaldehyde as ligand:: Synthesis and derivatization of carbonyl complexes [J].
Alvarez, Celedonio M. ;
Garcia-Rodriguez, Raul ;
Miguel, Daniel .
DALTON TRANSACTIONS, 2007, (32) :3546-3554
[7]   Stereoselective Aldol Addition to Rhenium(I) Complexes and Reversible Dimerization with Epimerization of the Metal Center [J].
Alvarez, Celedonio M. ;
Carrillo, Romen ;
Garcia-Rodriguez, Raul ;
Miguel, Daniel .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (25) :8285-8293
[8]   Intramolecular carboboration of carbonyl ligands to form boroxycarbenes [J].
Alvarez, Celedonio M. ;
Carrillo, Romen ;
Garcia-Rodriguez, Raul ;
Miguel, Daniel .
CHEMICAL COMMUNICATIONS, 2012, 48 (62) :7705-7707
[9]   Beyond click chemistry: spontaneous C-triazolyl transfer from copper to rhenium and transformation into mesoionic C-triazolylidene carbene [J].
Alvarez, Celedonio M. ;
Garcia-Escudero, Luis A. ;
Garcia-Rodriguez, Raul ;
Miguel, Daniel .
CHEMICAL COMMUNICATIONS, 2012, 48 (57) :7209-7211
[10]   Iminopyridine Complexes of Manganese, Rhenium, and Molybdenum Derived from Amino Ester Methylserine and Peptides Gly-Gly, Gly-Val, and Gly-Gly-Gly: Self-Assembly of the Peptide Chains [J].
Alvarez, Celedonio M. ;
Garcia-Rodriguez, Raul ;
Miguel, Daniel .
INORGANIC CHEMISTRY, 2012, 51 (05) :2984-2996