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1q74

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[[Image:1q74.gif|left|200px]]
[[Image:1q74.gif|left|200px]]
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{{Structure
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|PDB= 1q74 |SIZE=350|CAPTION= <scene name='initialview01'>1q74</scene>, resolution 1.70&Aring;
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The line below this paragraph, containing "STRUCTURE_1q74", creates the "Structure Box" on the page.
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|LIGAND= <scene name='pdbligand=PE4:2-{2-[2-(2-{2-[2-(2-ETHOXY-ETHOXY)-ETHOXY]-ETHOXY}-ETHOXY)-ETHOXY]-ETHOXY}-ETHANOL'>PE4</scene>, <scene name='pdbligand=ZN:ZINC+ION'>ZN</scene>
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|GENE= Rv1170 ([http://www.ncbi.nlm.nih.gov/Taxonomy/Browser/wwwtax.cgi?mode=Info&srchmode=5&id=1773 Mycobacterium tuberculosis])
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|DOMAIN=<span class='plainlinks'>[http://www.ncbi.nlm.nih.gov/Structure/cdd/cddsrv.cgi?uid=COG2120 COG2120]</span>
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{{STRUCTURE_1q74| PDB=1q74 | SCENE= }}
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|RESOURCES=<span class='plainlinks'>[http://oca.weizmann.ac.il/oca-docs/fgij/fg.htm?mol=1q74 FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=1q74 OCA], [http://www.ebi.ac.uk/pdbsum/1q74 PDBsum], [http://www.rcsb.org/pdb/explore.do?structureId=1q74 RCSB]</span>
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'''The Crystal Structure of 1D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside Deacetylase (MshB)'''
'''The Crystal Structure of 1D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside Deacetylase (MshB)'''
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sat May 3 05:57:02 2008''
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sun Mar 30 23:09:42 2008''
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Revision as of 02:57, 3 May 2008

Image:1q74.gif

Template:STRUCTURE 1q74

The Crystal Structure of 1D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside Deacetylase (MshB)


Overview

The C2-symmetric vinyl sulfoxide, trans-2-methylene-1,3-dithiolane 1,3-dioxide, was found to react with a range of 3-oxidopyridinium betaines (bearing different substituents on nitrogen) in high yield and with total diastereoselectivity. A 2.3:1 mixture of regioisomers was formed with all of the 3-oxidopyridinium betaines but the ratio was found to change over prolonged periods of time due to reversibility of the minor regioisomer. 3-Oxidopyridinium betaines bearing methyl substituents at either the 2- or 6-position were also tested in the cycloaddition process. Improved regioselectivity (8:1) and again high diastereoselectivity were observed with the betaine having an additional substituent at the 2-position, but with betaines having a substituent in the 6-position although high regioselectivity was observed (9.9:1), the major isomer was formed with low diastereoselectivity (5.5:4.4). The origin of the regio- and diastereo-selectivity with all the betaines is discussed. Finally, the C2-symmetric vinyl sulfoxide, trans-2-methylene-1,3-dithiolane 1,3-dioxide was reacted with an oxidopyrylium betaine in moderate yield. Good regioselectivity and moderate diastereoselectivity were observed.

About this Structure

1Q74 is a Single protein structure of sequence from Mycobacterium tuberculosis. Full crystallographic information is available from OCA.

Reference

Highly diastereoselective 1,3-dipolar cycloaddition reactions of trans-2-methylene-1,3-dithiolane 1,3-dioxide with 3-oxidopyridinium and 3-oxidopyrylium betaines: a route to the tropane skeleton., Aggarwal VK, Grainger RS, Newton GK, Spargo PL, Hobson AD, Adams H, Org Biomol Chem. 2003 Jun 7;1(11):1884-93. PMID:12945769 Page seeded by OCA on Sat May 3 05:57:02 2008

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