Synthesis of chiral amino acids with metal ion chelating side chains from L-serine using Negishi cross-coupling reaction

Kruppa, Michael and Imperato, Giovanni and Koenig, Burkhard (2006) Synthesis of chiral amino acids with metal ion chelating side chains from L-serine using Negishi cross-coupling reaction. TETRAHEDRON, 62 (7). pp. 1360-1364. ISSN 0040-4020,

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Abstract

The scope of the Negishi cross-coupling reaction of organozinc compounds derived from chiral amino acids was extended to electron rich iodoanilines and iodobenzylamines as coupling reagents. The protocol allows the direct modification of serine into phenylalanine derivatives bearing metal ion chelating ligands in their side chain, such as amino esters 6 and 7. The preparation of metal complex labeled peptides, the construction of synthetic receptors and hybrid materials are potential applications of the modified chiral amino acids. (c) 2005 Elsevier Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: BETA-STRAND; ORGANOZINC CHEMISTRY; SECONDARY STRUCTURE; LIGATING RESIDUES; L-PHENYLALANINE; HELIX BUNDLES; PRION PROTEIN; SCRAPIE PRION; ALPHA-AMINO; PEPTIDES; amino acids; metal chelates; organozinc compounds; C-C bond formation; Negishi coupling
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 22 Feb 2021 14:07
Last Modified: 22 Feb 2021 14:07
URI: https://pred.uni-regensburg.de/id/eprint/34943

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