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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3947

Title: Mimicking the Intradiol Catechol Cleavage Activity of Catechol Dioxygenase by High-Spin Iron(III) Complexes of a New Class of a Facially Bound [N(2)O] Ligand
Authors: PANDA, MK
JOHN, A
SHAIKH, MM
GHOSH, P
Keywords: nonheme iron enzymes
functional models
protocatechuate 3,4-dioxygenase
crystal-structures
cleaving dioxygenases
tridentate ligands
catalytic-activity
substrate complex
binding-site
3n ligands
Issue Date: 2008
Publisher: AMER CHEMICAL SOC
Citation: INORGANIC CHEMISTRY, 47(24), 11847-11856
Abstract: A series of high-spin iron(III) complexes, {N-R-2-[(pyridin-2-ylmethyl)amino]acetamide}FeCl(3) [R = mesityl (1b), 2,6-Et(2)C(6)H(3) (2b), and 2,6-i-Pr(2)C(6)H(3) (3b)], that functionally emulate the intradiol catechol dioxygenase enzyme are reported. In particular, these enzyme mimics, 1b, 2b, and 3b, which utilized molecular oxygen in carrying out the intradiol catechol cleavage of 3,5-di-tert-butylcatechol with high regioselectivity. (ca. 81-85%) at room temperature under ambient conditions, were designed by employing a new class of a facially bound [N(2)O] ligand, namely, N-R-2-[(pyridin-2-ylmethyl)amino]acetamide [R = mesityl (1a), 2,6-Et(2)C(6)H(3) (2a), and 2,6-i-Pr(2)C(6)H(3) (3a)]. The density functional theory studies revealed that the intradiol catechol cleavage reaction proceeded by an iron(III) peroxo intermediate that underwent 1,2-Criegee rearrangement to yield the intradiol catechol cleaved products analogous to the native enzyme.
URI: http://dx.doi.org/10.1021/ic801576f
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3947
http://hdl.handle.net/10054/3947
ISSN: 0020-1669
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