| A possible hydrolysis mechanism of beta-naphthyl acetate catalyzed by antibodies. | |
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MedLine Citation:
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PMID: 9791735 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The mechanism of ester hydrolysis has been extensively studied; however, the precise function of active-site residues in promoting catalysis is unclear. We describe here the structural models for the complex of a catalytic antibody Fv fragment with a phosphonate transition-state analogue, constructed by using gene cloning, sequencing and molecular modeling, mainly based on a known X-ray structure of a catalytic antibody. Hydrophobic and electrostatic analyses of the Fv/analog and Fv/substrate interaction suggest the hydrolysis mechanism: Tyr L91 and Tyr H97 play important roles to stabilize the beta-naphthyl group of hapten through pi-stack; His H35 donates a pair of free electrons at the atom NE2 to an active water and let it to be a partial hydroxide, which attacks the carbon atom of the carbonyl group of the substrate. Both His H35 and Arg L96 can form hydrogen bonds and stabilize the anionic tetrahedral intermediate formed during turnover. This mechanism emphasizes that an active water bridge may be formed during hydrolysis process. |
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Authors:
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Y R Yuan; Z X Xia; C H Yang; B H Yang; M Yeh |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Cell research Volume: 8 ISSN: 1001-0602 ISO Abbreviation: Cell Res. Publication Date: 1998 Sep |
Date Detail:
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Created Date: 1998-12-14 Completed Date: 1998-12-14 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9425763 Medline TA: Cell Res Country: CHINA |
Other Details:
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Languages: eng Pagination: 219-30 Citation Subset: IM |
Affiliation:
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Shanghai Institute of Cell Biology, Chinese Academy of Sciences, China. imceng@server.shcnc.ac.cn |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acid Sequence Animals Antibodies, Monoclonal / chemistry, genetics, metabolism* Base Sequence Binding Sites, Antibody / immunology Catalysis Cell Line Cloning, Molecular Computer Simulation Genes, Immunoglobulin / genetics Haptens / immunology, metabolism Hybridomas Hydrolysis Immunoglobulin Heavy Chains / genetics Immunoglobulin Light Chains / genetics Immunoglobulin Variable Region / genetics Models, Molecular Molecular Sequence Data Naphthols / chemistry, metabolism* Sequence Homology, Amino Acid |
| Chemical | |
Reg. No./Substance:
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0/Antibodies, Monoclonal; 0/Binding Sites, Antibody; 0/Haptens; 0/Immunoglobulin Heavy Chains; 0/Immunoglobulin Light Chains; 0/Immunoglobulin Variable Region; 0/Naphthols; 29692-55-5/naphthyl acetate |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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