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Syntheses, X-ray, MSn, NMR and CD structure determination of nickel(II) complexes of Schiff bases of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and aromatic α-amino acids

Milan Nadvornik ; Vratislav Langer (Institutionen för kemi- och bioteknik, Oorganisk miljökemi) ; Robert Jirasko ; Michal Holcapek ; Tomas Weidlich ; Antonin Lycka ; Alexander Popkov
Polyhedron (0277-5387). Vol. 27 (2008), 17, p. 3477-3483.
[Artikel, refereegranskad vetenskaplig]

A preparative procedure for the synthesis of an important chiral synthon of side-chain protected tyrosine was developed and optimised for the minimisation of nickel salts waste. While preparing a similar side-chain protected tryptophan synthon, an unexpected low stability was found of the Boc-protective group of the tryptophan aromatic nitrogen during purification on silica gel. X-ray crystal structure determination, tandem mass spectrometry (MS/MS) and NMR were applied for the elucidation of the structures of the prepared complexes and by-products. Stereochemistry of products of α-methylation of the complexes was assessed using a model tyrosine-derived compound.

Nyckelord: Nickel, Schiff base, alpha-methyl amino acids, chiral synthon, protective groups, circular dichroism



Denna post skapades 2008-11-19. Senast ändrad 2013-05-28.
CPL Pubid: 78334

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Oorganisk miljökemi (2005-2014)

Ämnesområden

Koordinationskemi
Fasta tillståndets kemi
Bio-oorganisk kemi
Organisk syntes
Bioorganisk kemi
Miljötoxikologi
Läkemedelskemi

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