Document Detail


Selective catalysis with peptide dendrimers.
MedLine Citation:
PMID:  15212529     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Peptide dendrimers incorporating 3,5-diaminobenzoic acid 1 as a branching unit (B) were prepared by solid-phase synthesis of ((Ac-A(3))(2)B-A(2))(2)B-Cys-A(1)-NH(2) followed by disulfide bridge formation. Twenty-one homo- and heterodimeric dendrimers were obtained by permutations of aspartate, histidine, and serine at positions A(1), A(2), and A(3). Two dendrimers catalyzed the hydrolysis of 7-hydroxy-N-methyl-quinolinium esters (2-5), and two other dendrimers catalyzed the hydrolysis of 8-hydroxy-pyrene-1,3,6-trisulfonate esters (10-12). Enzyme-like kinetics was observed in aqueous buffer pH 6.0 with multiple turnover, substrate binding (K(M) = 0.1-0.5 mM), rate acceleration (k(cat)/k(uncat) > 10(3)), and chiral discrimination (E = 2.8 for 2-phenylpropionate ester 5). The role of individual amino acids in catalysis was investigated by amino acid exchanges, highlighting the key role of histidine as a catalytic residue, and the importance of electrostatic and hydrophobic interactions in modulating substrate binding. These experiments demonstrate for the first time selective catalysis in peptide dendrimers.
Authors:
Céline Douat-Casassus; Tamis Darbre; Jean-Louis Reymond
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  126     ISSN:  0002-7863     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2004 Jun 
Date Detail:
Created Date:  2004-06-23     Completed Date:  2004-09-07     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7817-26     Citation Subset:  IM    
Affiliation:
Department of Chemistry & Biochemistry, University of Berne, Freiestrasse 3, CH-3012 Berne, Switzerland.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry
Aminobenzoic Acids / chemistry
Binding Sites
Catalysis
Esters / chemistry
Histidine / chemistry
Hydrogen-Ion Concentration
Hydrolysis
Hydrophobicity
Kinetics
Models, Chemical
Peptides / chemical synthesis*,  metabolism
Polymers / chemistry*,  metabolism
Quinolinium Compounds / chemistry
Static Electricity
Substrate Specificity
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Aminobenzoic Acids; 0/Esters; 0/Peptides; 0/Polymers; 0/Quinolinium Compounds; 535-87-5/3,5-diaminobenzoic acid; 71-00-1/Histidine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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