1riw

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[[Image:1riw.gif|left|200px]]
[[Image:1riw.gif|left|200px]]
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{{Structure
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<!--
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|PDB= 1riw |SIZE=350|CAPTION= <scene name='initialview01'>1riw</scene>, resolution 2.04&Aring;
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The line below this paragraph, containing "STRUCTURE_1riw", 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=NA:SODIUM+ION'>NA</scene>, <scene name='pdbligand=NAG:N-ACETYL-D-GLUCOSAMINE'>NAG</scene>, <scene name='pdbligand=OSC:(2R,3AS,6R,7AS)-N-(2-{1-[AMINO(IMINO)METHYL]-2,5-DIHYDRO-1H-PYRROL-3-YL}ETHYL)-6-HYDROXY-1-{N-[(2S)-2-HYDROXY-3-PHENYLPROPANOYL]PHENYLALANYL}OCTAHYDRO-1H-INDOLE-2-CARBOXAMIDE'>OSC</scene>, <scene name='pdbligand=SO4:SULFATE+ION'>SO4</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/Thrombin Thrombin], with EC number [http://www.brenda-enzymes.info/php/result_flat.php4?ecno=3.4.21.5 3.4.21.5] </span>
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or leave the SCENE parameter empty for the default display.
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|GENE=
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-->
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|DOMAIN=
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{{STRUCTURE_1riw| PDB=1riw | 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=1riw FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=1riw OCA], [http://www.ebi.ac.uk/pdbsum/1riw PDBsum], [http://www.rcsb.org/pdb/explore.do?structureId=1riw RCSB]</span>
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}}
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'''Thrombin in complex with natural product inhibitor Oscillarin'''
'''Thrombin in complex with natural product inhibitor Oscillarin'''
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[[Category: Petersen, J F.W.]]
[[Category: Petersen, J F.W.]]
[[Category: Tremblay, M.]]
[[Category: Tremblay, M.]]
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[[Category: inhibitor complex]]
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[[Category: Inhibitor complex]]
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[[Category: oscillarin]]
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[[Category: Oscillarin]]
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[[Category: protease]]
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[[Category: Protease]]
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[[Category: thrombin]]
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[[Category: Thrombin]]
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sat May 3 07:33:10 2008''
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sun Mar 30 23:28:46 2008''
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Revision as of 04:33, 3 May 2008

Image:1riw.gif

Template:STRUCTURE 1riw

Thrombin in complex with natural product inhibitor Oscillarin


Overview

The first enantiocontrolled total synthesis of the marine natural product oscillarin is described. The proposed structure and absolute configuration of oscillarin is thus confirmed, and a previously assigned structure of a subunit was shown to be incorrect. The X-ray structure of an oscillarin-thrombin complex was resolved at 2.0 A resolution, which validated its potent inhibitory activity against the enzyme with an IC(50) = 28 nM. Methodology was developed for the synthesis of enantiopure octahydroindole-2-carboxylic acids with usable functionality at C-6. The method consists of the halocarbocyclization of N-acyloxyiminium ions containing an olefinic tether in the presence of tin tetrachloride or tin tetrabromide. This N-acyloxyiminium ion aza-Prins carbocyclization proved to be general for the construction of octahydroindole and perhydroquinoline 2-carboxylic acids. Mechanistic rationales are based on an antiperiplanar attack of the terminal alkene on the iminium ion, leading to an incipient secondary carbocation which is trapped by halide via an equatorial attack. X-ray crystal structures of products corroborate the expected stereochemistry.

About this Structure

1RIW is a Protein complex structure of sequences from Homo sapiens. Full crystallographic information is available from OCA.

Reference

The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin., Hanessian S, Tremblay M, Petersen JF, J Am Chem Soc. 2004 May 19;126(19):6064-71. PMID:15137772 Page seeded by OCA on Sat May 3 07:33:10 2008

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