1ys1
From Proteopedia
(New page: 200px<br /><applet load="1ys1" size="450" color="white" frame="true" align="right" spinBox="true" caption="1ys1, resolution 1.10Å" /> '''Burkholderia cepacia...) |
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| - | [[Image:1ys1.gif|left|200px]]<br /><applet load="1ys1" size=" | + | [[Image:1ys1.gif|left|200px]]<br /><applet load="1ys1" size="350" color="white" frame="true" align="right" spinBox="true" |
caption="1ys1, resolution 1.10Å" /> | caption="1ys1, resolution 1.10Å" /> | ||
'''Burkholderia cepacia lipase complexed with hexylphosphonic acid (R)-2-methyl-3-phenylpropyl ester'''<br /> | '''Burkholderia cepacia lipase complexed with hexylphosphonic acid (R)-2-methyl-3-phenylpropyl ester'''<br /> | ||
==Overview== | ==Overview== | ||
| - | Synthetic chemists often exploit the high enantioselectivity of lipases to | + | Synthetic chemists often exploit the high enantioselectivity of lipases to prepare pure enantiomers of primary alcohols, but the molecular basis for this enantioselectivity is unknown. The crystal structures of two phosphonate transition-state analogs bound to Burkholderia cepacia lipase reveal this molecular basis for a typical primary alcohol: 2-methyl-3-phenyl-1-propanol. The enantiomeric alcohol moieties adopt surprisingly similar orientations, with only subtle differences that make it difficult to predict how to alter enantioselectivity. These structures, along with a survey of previous structures of enzyme bound enantiomers, reveal that binding of enantiomers does not involve an exchange of two substituent positions as most researchers assumed. Instead, the enantiomers adopt mirror-image packing, where three of the four substituents at the stereocenter lie in similar positions. The fourth substituent, hydrogen, points in opposite directions. |
==About this Structure== | ==About this Structure== | ||
| - | 1YS1 is a [http://en.wikipedia.org/wiki/Single_protein Single protein] structure of sequence from [http://en.wikipedia.org/wiki/Burkholderia_cepacia Burkholderia cepacia] with CA and 2HR as [http://en.wikipedia.org/wiki/ligands ligands]. Active as [http://en.wikipedia.org/wiki/Triacylglycerol_lipase Triacylglycerol lipase], with EC number [http://www.brenda-enzymes.info/php/result_flat.php4?ecno=3.1.1.3 3.1.1.3] Full crystallographic information is available from [http:// | + | 1YS1 is a [http://en.wikipedia.org/wiki/Single_protein Single protein] structure of sequence from [http://en.wikipedia.org/wiki/Burkholderia_cepacia Burkholderia cepacia] with <scene name='pdbligand=CA:'>CA</scene> and <scene name='pdbligand=2HR:'>2HR</scene> as [http://en.wikipedia.org/wiki/ligands ligands]. Active as [http://en.wikipedia.org/wiki/Triacylglycerol_lipase Triacylglycerol lipase], with EC number [http://www.brenda-enzymes.info/php/result_flat.php4?ecno=3.1.1.3 3.1.1.3] Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1YS1 OCA]. |
==Reference== | ==Reference== | ||
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[[Category: Single protein]] | [[Category: Single protein]] | ||
[[Category: Triacylglycerol lipase]] | [[Category: Triacylglycerol lipase]] | ||
| - | [[Category: Cheong, C | + | [[Category: Cheong, C S.]] |
| - | [[Category: Kazlauskas, R | + | [[Category: Kazlauskas, R J.]] |
[[Category: Mezzetti, A.]] | [[Category: Mezzetti, A.]] | ||
| - | [[Category: Schrag, J | + | [[Category: Schrag, J D.]] |
[[Category: 2HR]] | [[Category: 2HR]] | ||
[[Category: CA]] | [[Category: CA]] | ||
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[[Category: inhibitor hexylphosphonic acid (r) 2-methyl-3-phenylpropyl ester]] | [[Category: inhibitor hexylphosphonic acid (r) 2-methyl-3-phenylpropyl ester]] | ||
| - | ''Page seeded by [http:// | + | ''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Thu Feb 21 16:08:34 2008'' |
Revision as of 14:08, 21 February 2008
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Burkholderia cepacia lipase complexed with hexylphosphonic acid (R)-2-methyl-3-phenylpropyl ester
Overview
Synthetic chemists often exploit the high enantioselectivity of lipases to prepare pure enantiomers of primary alcohols, but the molecular basis for this enantioselectivity is unknown. The crystal structures of two phosphonate transition-state analogs bound to Burkholderia cepacia lipase reveal this molecular basis for a typical primary alcohol: 2-methyl-3-phenyl-1-propanol. The enantiomeric alcohol moieties adopt surprisingly similar orientations, with only subtle differences that make it difficult to predict how to alter enantioselectivity. These structures, along with a survey of previous structures of enzyme bound enantiomers, reveal that binding of enantiomers does not involve an exchange of two substituent positions as most researchers assumed. Instead, the enantiomers adopt mirror-image packing, where three of the four substituents at the stereocenter lie in similar positions. The fourth substituent, hydrogen, points in opposite directions.
About this Structure
1YS1 is a Single protein structure of sequence from Burkholderia cepacia with and as ligands. Active as Triacylglycerol lipase, with EC number 3.1.1.3 Full crystallographic information is available from OCA.
Reference
Mirror-image packing in enantiomer discrimination molecular basis for the enantioselectivity of B.cepacia lipase toward 2-methyl-3-phenyl-1-propanol., Mezzetti A, Schrag JD, Cheong CS, Kazlauskas RJ, Chem Biol. 2005 Apr;12(4):427-37. PMID:15850979
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