| 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 |
Related Documents
:
|
767339 - Stoichiometry of polypeptide chain elongation. 4992319 - Possible inhibitory effect of teichoic acid on bacillus subtilis transfer ribonucleic a... 4622829 - Analysis of free amino acid pools in fungal mycelia. 11152299 - Conformational restriction of the tyr53 side-chain in the decapeptide he. 5500319 - The effect of hypermethylation on the functional properties of transfer ribonucleic aci... 17066369 - Collision-induced dissociation of protonated tetrapeptides containing beta-alanine, gam... 17317159 - Citric acid production by a novel aspergillus niger isolate: ii. optimization of proces... 17965709 - Control of protein phosphorylation with a genetically encoded photocaged amino acid. 16610779 - Identification of ellagic acid as potent inhibitor of protein kinase ck2: a successful ... |
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. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| 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
Previous Document: A cubic arrangement of DNA double helices based on nickel-guanine interactions.
Next Document: Molecular imprinting made easy.