Chapter title |
4-Fluoroprolines: Conformational Analysis and Effects on the Stability and Folding of Peptides and Proteins
|
---|---|
Chapter number | 196 |
Book title |
Peptidomimetics I
|
Published in |
Topics in heterocyclic chemistry, January 2016
|
DOI | 10.1007/7081_2015_196 |
Pubmed ID | |
Book ISBNs |
978-3-31-949117-2, 978-3-31-949119-6
|
Authors |
Robert W. Newberry, Ronald T. Raines |
Abstract |
Proline is unique among proteinogenic amino acids because a pyrrolidine ring links its amino group to its side chain. This heterocycle constrains the conformations of the main chain and thus templates particular secondary structures. Proline residues undergo post-translational modification at the 4-position to yield 4-hydroxyproline, which is especially prevalent in collagen. Interest in characterizing the effects of this modification led to the use of 4-fluoroprolines to enhance inductive properties relative to the hydroxyl group of 4-hydroxyproline and to eliminate contributions from hydrogen bonding. The strong inductive effect of the fluoro group has three main consequences: enforcing a particular pucker upon the pyrrolidine ring, biasing the conformation of the preceding peptide bond, and accelerating cis/trans prolyl peptide bond isomerization. These subtle, yet reliable modulations make 4-fluoroproline-incorporation a complement to traditional genetic approaches for exploring structure-function relationships in peptides and proteins, as well as for endowing peptides and proteins with conformational stability. |
Mendeley readers
Geographical breakdown
Country | Count | As % |
---|---|---|
Unknown | 34 | 100% |
Demographic breakdown
Readers by professional status | Count | As % |
---|---|---|
Student > Master | 6 | 18% |
Student > Doctoral Student | 4 | 12% |
Researcher | 4 | 12% |
Student > Ph. D. Student | 3 | 9% |
Other | 2 | 6% |
Other | 1 | 3% |
Unknown | 14 | 41% |
Readers by discipline | Count | As % |
---|---|---|
Chemistry | 12 | 35% |
Biochemistry, Genetics and Molecular Biology | 2 | 6% |
Agricultural and Biological Sciences | 2 | 6% |
Medicine and Dentistry | 2 | 6% |
Pharmacology, Toxicology and Pharmaceutical Science | 1 | 3% |
Other | 1 | 3% |
Unknown | 14 | 41% |