| Molecular recognition by secondary metabolites. | |
| | |
MedLine Citation:
|
PMID: 2372307 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
Aspects of molecular recognition based on the interaction between the vancomycin group of antibiotics and bacterial cell wall precursor analogues are discussed. The energetically unfavourable folding-in of the residue 1 sidechain in vancomycin and ristocetin A is discussed in terms of the favourable entropy associated with simultaneous release of solvent molecules. The effect of the sugar amino substituent on the strength of an adjacent hydrophobic interaction in the vancomycin/acetyl-D-Ala-D-Ala complex is rationalised as an intramolecular "salting-out" of hydrocarbon entities. The slow on-rate for dimerisation of the ristocetin A/N,N-diacetyl-L-Lys-D-Ala-D-Ala complex is attributed to the need for the relatively rigid peptide backbone of the antibiotic to be extensively desolvated before dimerisation can occur. Some of these concepts are then applied to understanding the interactions between antibiotics and the minor groove of double-helical DNA, the receptor site with which they have probably evolved to interact. Two structural motifs (pi-polarised aromatic rings and deoxy sugars) are postulated to be important in this recognition process. The possible roles of these structural features are discussed. |
| | |
Authors:
|
D H Williams; M J Stone; R J Mortishire-Smith; P R Hauck |
Related Documents
:
|
17090667 - Combinatorial biosynthesis of novel antibiotics related to daptomycin. 1901657 - Product of the pseudomonas aeruginosa gene pild is a prepilin leader peptidase. 20410587 - Inhibition of septation in bacillus subtilis by a peptide antibiotic, edeine b(1). 19758327 - Tyrosine 9 is the key amino acid in microcin j25 superoxide overproduction. 3594477 - A comparative 1h-n.m.r. study of murnac-l-ala-d-igln (mdp) and its analogue murabutide:... 20201807 - Conformations and biological activities of amyloid beta peptide 25-35. |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
|
Title: Biochemical pharmacology Volume: 40 ISSN: 0006-2952 ISO Abbreviation: Biochem. Pharmacol. Publication Date: 1990 Jul |
Date Detail:
|
Created Date: 1990-08-21 Completed Date: 1990-08-21 Revised Date: 2006-11-15 |
Medline Journal Info:
|
Nlm Unique ID: 0101032 Medline TA: Biochem Pharmacol Country: ENGLAND |
Other Details:
|
Languages: eng Pagination: 27-34 Citation Subset: IM |
Affiliation:
|
University Chemical Laboratory, Cambridge, U.K. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Aminoglycosides Anti-Bacterial Agents / metabolism* Base Sequence Binding Sites DNA / metabolism* Membrane Proteins / metabolism Molecular Sequence Data Peptides Protein Conformation Ristocetin / metabolism Structure-Activity Relationship Vancomycin / metabolism |
| Chemical | |
Reg. No./Substance:
|
0/Aminoglycosides; 0/Anti-Bacterial Agents; 0/Membrane Proteins; 0/Peptides; 11021-66-2/ristocetin A; 1404-55-3/Ristocetin; 1404-90-6/Vancomycin; 9007-49-2/DNA |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Heteronuclear 3D NMR and isotopic labeling of calmodulin. Towards the complete assignment of the 1H ...
Next Document: Structure-function relationships in epidermal growth factor (EGF) and transforming growth factor-alp...