1q74
From Proteopedia
(New page: 200px<br /><applet load="1q74" size="450" color="white" frame="true" align="right" spinBox="true" caption="1q74, resolution 1.70Å" /> '''The Crystal Structur...) |
|||
| Line 1: | Line 1: | ||
| - | [[Image:1q74.gif|left|200px]]<br /><applet load="1q74" size=" | + | [[Image:1q74.gif|left|200px]]<br /><applet load="1q74" size="350" color="white" frame="true" align="right" spinBox="true" |
caption="1q74, resolution 1.70Å" /> | caption="1q74, resolution 1.70Å" /> | ||
'''The Crystal Structure of 1D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside Deacetylase (MshB)'''<br /> | '''The Crystal Structure of 1D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside Deacetylase (MshB)'''<br /> | ||
==Overview== | ==Overview== | ||
| - | The C2-symmetric vinyl sulfoxide, trans-2-methylene-1,3-dithiolane | + | 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== | ==About this Structure== | ||
| - | 1Q74 is a [http://en.wikipedia.org/wiki/Single_protein Single protein] structure of sequence from [http://en.wikipedia.org/wiki/Mycobacterium_tuberculosis Mycobacterium tuberculosis] with ZN and PE4 as [http://en.wikipedia.org/wiki/ligands ligands]. Full crystallographic information is available from [http:// | + | 1Q74 is a [http://en.wikipedia.org/wiki/Single_protein Single protein] structure of sequence from [http://en.wikipedia.org/wiki/Mycobacterium_tuberculosis Mycobacterium tuberculosis] with <scene name='pdbligand=ZN:'>ZN</scene> and <scene name='pdbligand=PE4:'>PE4</scene> as [http://en.wikipedia.org/wiki/ligands ligands]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1Q74 OCA]. |
==Reference== | ==Reference== | ||
| Line 15: | Line 15: | ||
[[Category: Arad, D.]] | [[Category: Arad, D.]] | ||
[[Category: Av-Gay, Y.]] | [[Category: Av-Gay, Y.]] | ||
| - | [[Category: Cherney, M | + | [[Category: Cherney, M M.]] |
| - | [[Category: Fahey, R | + | [[Category: Fahey, R C.]] |
[[Category: Garen, C.]] | [[Category: Garen, C.]] | ||
| - | [[Category: James, M | + | [[Category: James, M N.]] |
| - | [[Category: Maynes, J | + | [[Category: Maynes, J T.]] |
[[Category: Newton, G.]] | [[Category: Newton, G.]] | ||
| - | [[Category: TBSGC, TB | + | [[Category: TBSGC, TB Structural Genomics Consortium.]] |
[[Category: PE4]] | [[Category: PE4]] | ||
[[Category: ZN]] | [[Category: ZN]] | ||
| Line 32: | Line 32: | ||
[[Category: zinc aminohydrolase]] | [[Category: zinc aminohydrolase]] | ||
| - | ''Page seeded by [http:// | + | ''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Thu Feb 21 14:36:34 2008'' |
Revision as of 12:36, 21 February 2008
|
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 with and as ligands. 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 Thu Feb 21 14:36:34 2008
Categories: Mycobacterium tuberculosis | Single protein | Arad, D. | Av-Gay, Y. | Cherney, M M. | Fahey, R C. | Garen, C. | James, M N. | Maynes, J T. | Newton, G. | TBSGC, TB Structural Genomics Consortium. | PE4 | ZN | Protein structure initiative | Psi | Rossmann fold | Structural genomics | Tb structural genomics consortium | Tbsgc | Zinc aminohydrolase
