1w3v

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[[Image:1w3v.gif|left|200px]]
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{{Seed}}
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{{STRUCTURE_1w3v| PDB=1w3v | SCENE= }}
{{STRUCTURE_1w3v| PDB=1w3v | SCENE= }}
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'''ISOPENICILLIN N SYNTHASE D-(L-A-AMINOADIPOYL)-(3R)-METHYL-L-CYSTEINE D-A-HYDROXYISOVALERYL ESTER COMPLEX (ANAEROBIC)'''
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===ISOPENICILLIN N SYNTHASE D-(L-A-AMINOADIPOYL)-(3R)-METHYL-L-CYSTEINE D-A-HYDROXYISOVALERYL ESTER COMPLEX (ANAEROBIC)===
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==Overview==
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Isopenicillin N synthase (IPNS) is a non-heme iron(ii)-dependent oxidase that is central to penicillin biosynthesis. Herein, we report mechanistic studies of the IPNS reaction in the crystalline state, using the substrate analogue delta-(L-alpha-aminoadipoyl)-(3R)-methyl-L-cysteine D-alpha-hydroxyisovaleryl ester (AmCOV) to probe the early stages of the catalytic cycle. The X-ray crystal structure of the anaerobic IPNS:Fe(II):AmCOV complex was solved to 1.40 A resolution, and it reveals several subtle differences in the active site relative to the complex of the enzyme with its natural substrate. The crystalline IPNS:Fe(II):AmCOV complex was then exposed to oxygen gas at high pressure; this brought about reaction to give what appears to be a hydroxymethyl/ene-thiol product. A mechanism for this reaction is proposed. These results offer further insight into the delicate interplay of steric and electronic effects in the IPNS active site and the mechanistic intricacies of this remarkable enzyme.
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(as it appears on PubMed at http://www.pubmed.gov), where 16444759 is the PubMed ID number.
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{{ABSTRACT_PUBMED_16444759}}
==About this Structure==
==About this Structure==
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[[Category: Oxygenase]]
[[Category: Oxygenase]]
[[Category: Penicillin biosynthesis]]
[[Category: Penicillin biosynthesis]]
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sat May 3 13:07:18 2008''
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Tue Jul 29 02:32:59 2008''

Revision as of 23:33, 28 July 2008

Image:1w3v.png

Template:STRUCTURE 1w3v

ISOPENICILLIN N SYNTHASE D-(L-A-AMINOADIPOYL)-(3R)-METHYL-L-CYSTEINE D-A-HYDROXYISOVALERYL ESTER COMPLEX (ANAEROBIC)

Template:ABSTRACT PUBMED 16444759

About this Structure

1W3V is a Single protein structure of sequence from Emericella nidulans. Full crystallographic information is available from OCA.

Reference

Unexpected oxidation of a depsipeptide substrate analogue in crystalline isopenicillin N synthase., Daruzzaman A, Clifton IJ, Adlington RM, Baldwin JE, Rutledge PJ, Chembiochem. 2006 Feb;7(2):351-8. PMID:16444759

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