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Published on: August 1, 2018
An evaluation of peptide-bond isosteres
Amit Choudhary1, Ronald T Raines
1Graduate Program in Biophysics, University of Wisconsin-Madison, Madison, WI 53706-1534, USA.
Chembiochem : a European Journal of Chemical Biology
|July 14, 2011
Summary
Peptide-bond isosteres like thioamides, esters, alkenes, and fluoroalkenes offer insights into protein structure and function. These modifications allow chemical biologists to explore new structure-function relationships and enhance peptide properties.
Area of Science:
- Biochemistry and Molecular Biology
- Medicinal Chemistry
- Chemical Biology
Background:
- Peptide bonds are fundamental to protein structure and function.
- Modifying peptide bonds can alter protein properties for research and therapeutic applications.
- Peptide-bond isosteres are analogs that mimic peptide bonds but possess distinct chemical characteristics.
Purpose of the Study:
- To examine the electronic, structural, and conformational attributes of four peptide-bond isosteres: thioamides, esters, alkenes, and fluoroalkenes.
- To compare the noncovalent interaction capabilities of these isosteres with the native peptide bond.
- To highlight the utility of these isosteres in uncovering novel structure-function relationships and engineering protein attributes.
Main Methods:
- Detailed examination of the electronic properties of isosteres.
- Analysis of the structural and conformational features of isosteres.
- Comparative assessment of noncovalent interactions mediated by isosteres versus peptide bonds.
Main Results:
- Thioamides, esters, alkenes, and fluoroalkenes exhibit unique electronic and conformational profiles compared to peptide bonds.
- The noncovalent interaction potential of each isostere varies, influencing their behavior in biological systems.
- These variations allow for fine-tuning of molecular interactions and protein properties.
Conclusions:
- Peptide-bond isosteres are valuable tools for deep interrogation of peptide and protein structure-function relationships.
- These isosteres can be used to amplify or attenuate specific chemical properties, enabling new applications in chemical biology.
- The strategic use of isosteres allows for the development of peptides and proteins with tailored and desirable attributes.
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