1mbb

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[[Image:1mbb.gif|left|200px]]
[[Image:1mbb.gif|left|200px]]
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{{Structure
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|PDB= 1mbb |SIZE=350|CAPTION= <scene name='initialview01'>1mbb</scene>, resolution 2.30&Aring;
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The line below this paragraph, containing "STRUCTURE_1mbb", creates the "Structure Box" on the page.
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|SITE=
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You may change the PDB parameter (which sets the PDB file loaded into the applet)
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|LIGAND= <scene name='pdbligand=EEB:URIDINE-DIPHOSPHATE-3(N-ACETYLGLUCOSAMINYL)BUTYRIC+ACID'>EEB</scene>, <scene name='pdbligand=FAD:FLAVIN-ADENINE+DINUCLEOTIDE'>FAD</scene>
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or the SCENE parameter (which sets the initial scene displayed when the page is loaded),
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|ACTIVITY= <span class='plainlinks'>[http://en.wikipedia.org/wiki/UDP-N-acetylmuramate_dehydrogenase UDP-N-acetylmuramate dehydrogenase], with EC number [http://www.brenda-enzymes.info/php/result_flat.php4?ecno=1.1.1.158 1.1.1.158] </span>
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|GENE=
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|DOMAIN=
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{{STRUCTURE_1mbb| PDB=1mbb | SCENE= }}
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|RELATEDENTRY=
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|RESOURCES=<span class='plainlinks'>[http://oca.weizmann.ac.il/oca-docs/fgij/fg.htm?mol=1mbb FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=1mbb OCA], [http://www.ebi.ac.uk/pdbsum/1mbb PDBsum], [http://www.rcsb.org/pdb/explore.do?structureId=1mbb RCSB]</span>
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'''OXIDOREDUCTASE'''
'''OXIDOREDUCTASE'''
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[[Category: Lees, W J.]]
[[Category: Lees, W J.]]
[[Category: Walsh, C T.]]
[[Category: Walsh, C T.]]
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[[Category: flavoenzyme]]
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[[Category: Flavoenzyme]]
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[[Category: oxidoreductase]]
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[[Category: Oxidoreductase]]
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sat May 3 00:51:10 2008''
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sun Mar 30 22:13:54 2008''
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Revision as of 21:51, 2 May 2008

Image:1mbb.gif

Template:STRUCTURE 1mbb

OXIDOREDUCTASE


Overview

UDP-N-acetylenolpyruvylglucosamine reductase (MurB), a peptidoglycan biosynthetic enzyme from Escherichia coli, reduces both (E)- and (Z)-isomers of enolbutyryl-UDP-GlcNAc, C4 analogs of the physiological C3 enolpyruvyl substrate, to UDP-methyl-N-acetylmuramic acid in the presence of NADPH. The X-ray crystal structure of the (E)-enolbutyryl-UDP-GlcNAc-MurB complex is similar to that of the enolpyruvyl-UDP-GlcNAc-MurB complex. In both structures the groups thought to be involved in hydride transfer to C3 and protonation at C2 of the enol ether substrate are arranged anti relative to the enol double bond. The stereochemical outcome of reduction of (E)-enolbutyryl-UDP-GlcNAc by NADPD in D2O is thus predicted to yield a (2R,3R)-dideuterio product. This was validated by conversion of the 2,3-dideuterio-UDP-methyl-N-acetylmuramic acid product to 2,3-dideuterio-2-hydroxybutyrate, which was shown to be (2R) by enzymatic analysis and (3R) by NMR comparison to authentic (2R,3R)- and (2R,3S)-2,3-dideuterio-2-hydroxybutyrate. Remarkably, the (E)-enolbutyryl-UDP-GlcNAc was found to partition between reduction to UDP-methyl-N-acetylmuramic and isomerization to the (Z)-substrate isomer in the MurB active site, indicative of a C2 carbanion/enol species that is sufficiently long-lived to rotate around the C2-C3 single bond during catalysis.

About this Structure

1MBB is a Single protein structure of sequence from Escherichia coli. Full crystallographic information is available from OCA.

Reference

(E)-enolbutyryl-UDP-N-acetylglucosamine as a mechanistic probe of UDP-N-acetylenolpyruvylglucosamine reductase (MurB)., Lees WJ, Benson TE, Hogle JM, Walsh CT, Biochemistry. 1996 Feb 6;35(5):1342-51. PMID:8634262 Page seeded by OCA on Sat May 3 00:51:10 2008

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