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Stabilizing Factors for Vanadium(IV) in Amavadin
Author(s) -
Hubregtse Ton,
Hanefeld Ulf,
Arends Isabel W. C. E.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601053
Subject(s) - chemistry , vanadium , substituent , ligand (biochemistry) , denticity , nitrone , amino acid , aqueous solution , alkylation , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , metal , cycloaddition , receptor , biochemistry
Six secondary N ‐hydroxy amino acids (amavadin‐based ligands) have been prepared through a strategy with nitrone reduction as its key step. Two of these amino acids are the new amavadin ligand analogues 4a and 4b containing either a phenyl or a benzyl group in combination with a small backbone substituent. In addition, the monoester 5 of the amavadin ligand as well as three N ‐alkylated N ‐hydroxy aminoacids 6 were prepared. Complexation studies with the new tri‐ and bidentate ligands using HRMS revealed that only amavadin and its two analogues with ligands 4a and 4b are stable in aqueous and aerobic environments and that the complexation of vanadium(IV) with ligands 5 and 6 does not lead to air‐stable vanadium(IV) non‐oxo compounds. An interesting spin‐off of the synthetic work on nitrones is an effective and easily applicable method for the synthesis of racemic N ‐hydroxy amino acid esters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)