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1a3l

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[[Image:1a3l.gif|left|200px]]
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{{STRUCTURE_1a3l| PDB=1a3l | SCENE= }}
{{STRUCTURE_1a3l| PDB=1a3l | SCENE= }}
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'''CATALYSIS OF A DISFAVORED REACTION: AN ANTIBODY EXO DIELS-ALDERASE-TSA-INHIBITOR COMPLEX AT 1.95 A RESOLUTION'''
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===CATALYSIS OF A DISFAVORED REACTION: AN ANTIBODY EXO DIELS-ALDERASE-TSA-INHIBITOR COMPLEX AT 1.95 A RESOLUTION===
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==Overview==
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A highly specific Diels-Alder protein catalyst was made by manipulating the antibody repertoire of the immune system. The catalytic antibody 13G5 catalyzes a disfavored exo Diels-Alder transformation in a reaction for which there is no natural enzyme counterpart and that yields a single regioisomer in high enantiomeric excess. The crystal structure of the antibody Fab in complex with a ferrocenyl inhibitor containing the essential haptenic core that elicited 13G5 was determined at 1.95 angstrom resolution. Three key antibody residues appear to be responsible for the observed catalysis and product control. Tyrosine-L36 acts as a Lewis acid activating the dienophile for nucleophilic attack, and asparagine-L91 and aspartic acid-H50 form hydrogen bonds to the carboxylate side chain that substitutes for the carbamate diene substrate. This hydrogen-bonding scheme leads to rate acceleration and also pronounced stereoselectivity. Docking experiments with the four possible ortho transition states of the reaction explain the specific exo effect and suggest that the (3R,4R)-exo stereoisomer is the preferred product.
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(as it appears on PubMed at http://www.pubmed.gov), where 9506943 is the PubMed ID number.
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{{ABSTRACT_PUBMED_9506943}}
==About this Structure==
==About this Structure==
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[[Category: Disfavored reaction]]
[[Category: Disfavored reaction]]
[[Category: Immunoglobulin]]
[[Category: Immunoglobulin]]
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Fri May 2 09:45:45 2008''
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Mon Jun 30 15:56:06 2008''

Revision as of 12:56, 30 June 2008

Image:1a3l.png

Template:STRUCTURE 1a3l

CATALYSIS OF A DISFAVORED REACTION: AN ANTIBODY EXO DIELS-ALDERASE-TSA-INHIBITOR COMPLEX AT 1.95 A RESOLUTION

Template:ABSTRACT PUBMED 9506943

About this Structure

1A3L is a Protein complex structure of sequences from Mus musculus. Full crystallographic information is available from OCA.

Reference

An antibody exo Diels-Alderase inhibitor complex at 1.95 angstrom resolution., Heine A, Stura EA, Yli-Kauhaluoma JT, Gao C, Deng Q, Beno BR, Houk KN, Janda KD, Wilson IA, Science. 1998 Mar 20;279(5358):1934-40. PMID:9506943

Page seeded by OCA on Mon Jun 30 15:56:06 2008

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