Influence of N-terminal residue stereochemistry on the prolyl amide geometry and the conformation of 5-tert-butylproline type VI β-turn mimics

Journal of Peptide Science

Volumn 7, Issue 2, 2001, Pages 92-104

  Li, Haitao ^a   Jiang, Xiaohui ^a   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

5 tert butylproline; Cis amide bond; Stereochemistry; Steric interactions; Type VI turn mimics

Indexed keywords

5 TERT BUTYLPROLINE; ACETAMIDE DERIVATIVE; ACETONITRILE; AMIDE; AMINO ACID DERIVATIVE; CARBONYL DERIVATIVE; CHLOROFORM; DIMETHYL SULFOXIDE; DIPEPTIDE DERIVATIVE; LEUCINE; PEPTIDE DERIVATIVE; PROLINE DERIVATIVE; PROTON; SOLVENT; UNCLASSIFIED DRUG; WATER;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL BINDING; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CIRCULAR DICHROISM; CIS ISOMER; CONFORMATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; GEOMETRY; HYDROGEN BOND; ISOMERISM; MOLECULAR INTERACTION; MOLECULAR MIMICRY; PRIORITY JOURNAL; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTRUM; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANS ISOMER;

AMIDES; CHLOROFORM; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; PEPTIDE BIOSYNTHESIS; PROLINE; PROTEIN CONFORMATION; STEREOISOMERISM;

EID: 0035098807     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.297     Document Type: Article

References (45)

1. Analysis and prediction of the different types of β-turn in proteins
2. Turns in peptides and proteins
3. Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics
4. Conformation analysis of dipeptide mimetics
5. Conformational analysis of reverse-turn constraints by N-methylation and N-hydroxylation of amide bonds in peptides and non-peptide mimetics
6. Conformational analysis of homochiral and heterochiral diprolines as β-turn-forming pepidomimetics: Unsubstituted and substituted models
7. Steric effects on the amide isomer equilibrium of prolyl peptides. Synthesis and conformational analysis of N-acetyl-5-tert-butylproline N′-methylamides
8. Alkyl 3-position substituents retard the isomerization of prolyl and hydroxyprolyl amides in water
9. Use of steric interactions to control peptide turn geometry. Synthesis of type VI β-turn mimics with 5-tert-butylproline
10. Steric effects of 5-tert-butylproline in dipeptide mimics of type VI β-turns
11. The effects of stereochemistry and sequences on 5-tert-butylproline type VI β-turn mimics
12. An examination of the steric effects of 5-tert-butylproline on the conformation of polyproline and the cooperative nature of type II to type I helical interconversion
13. Synthesis and solution properties of poly(2-methylproline)
14. 7 amide cis-isomer population
15. Enhancing the proline effect: Pseudoprolines for tailoring cis/trans isomerization
16. Unusual cis-trans isomerism in N-acetyl, N′-methylamide derivatives of syn- and anti-5-methylproline
17. A convenient synthesis of the conformationally constrained amino acid 5,5-dimethylproline
18. Retention of the cis proline conformation in tripeptide fragments of bovine pancreatic Ribonuclease A containing a non-natural proline analogue, 5,5-dimethylproline
19. 13C NMR studies
20. Conformation repliée à l'état solide de la N-pivaloyl-D-alanyl-L-proline N-isopropylamide
21. Stereochemical requirements for β-hairpin formation: Model studies with four-residue peptides and depsipeptides
22. 2 cyclic hexapeptides. Preferred β-turn conformers and implications for β-turns in proteins
23. Crystal structure and conformation of cyclo-(glycylprolylglycyl-D-alanylprolyl) containing 4 → 1 and 3 → 1 intramolecular hydrogen bonds
24. Solution conformation of cyclo-(Gly-Pro-Ser-d-Ala-Pro). Hydrogen-bonded reverse turns in cyclic pentapeptides
25. VI turns in peptides and proteins: A model peptide mimicry
26. Conformational rearrangements required of the V3 loop of HIV-1 gp 120 for proteolytic cleavage and infection
27. A mechanism for rotamase catalysis by the FK506 binding protein (FKBP)
28. The X-ray structure of a tetrapeptide bound to the active site of human cyclophilin A
29. Peptidyl-prolyl cis/trans isomerases and their effectors
30. Human and Escherichia coli cyclophilins: Sensitivity to inhibition
31. 5-tert-Butylproline
32. Differential side chain hydration in a linear peptide containing a type VI turn
33. Folding of immunogenic peptide fragments of proteins in water solution
34. Chain-folding initiation structures in Ribonuclease A: Conformational free energy calculations on Ac-Asn-Pro-Tyr-NHMe, Ac-Tyr-Pro-Asn-NHMe, and related peptides
35. Local control of peptide conformation: Stabilization of cis proline peptide bonds by aromatic proline interactions
36. Pro-D-NMe-amino acid and D-Pro-NMe-amino acid: Simple, efficient reverse-turn constraints
37. NHα, in a globular protein
38. Studies of theorical circular dichroism of polypeptides: Contributions of β-turns
39. Determination of protein secondary structure in solution by vacuum ultraviolet circular dichroism
40. Comparison of conformation and antimicrobial activity of synthetic analogs of Gramicidin S: Stereochemical consideration of the role of D-phenylalanine in the antibiotic
41. Circular dichroism of β turns in peptides and proteins
42. Solvent-dependent conformational distributions of some dipeptides
43. Conformations of cyclic heptapeptides: Crystal structure and computational studies of evolidine
44. The molecular structure of a dimer composed of the variable portions of the Bence-Jones protein REI refined at 2.0-Å resolution
45. Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three linked peptide units