Concept

Proline

Publications associées (40)

Pseudo-prolines: Reversible, conformational trap of cyclosporin C as novel concept for prodrug design

The selective and reversible insertion of pseudo-proline (PsiPro) Systems in cyclosporin C (CsC) featuring different C(2) substituents at the oxazolidine ring and its impact on the conformational and biological properties is described. The presence of a 5- ...

2004

Triple Quantum Decoherence under Multiple Refocusing: Slow Correlated Chemical Shift Modulations of C' and N Nuclei in Proteins

Geoffrey Bodenhausen, Julien Wist

A new expt. allows the identification of residues that feature slow conformational exchange in macromols. Rotations about dihedral angles that are slower than the global correlation time tc cause a modulation of the isotropic chem. shifts of the nuclei. If ...

2004

Pseudoproline libraries for tuning inhibitors of SH3 domain mediated protein-protein interactions

Luc Patiny, Patricia Durieux

A symposium report. Pseudoprolines such as Ser, Thr, Cys derived proline-ring structures with enhanced inherent properties of L-Pro were used to evaluate ligand receptor interaction of Pro-rich peptides. The generation of pseudoproline-libraries exhibiting ...

2001

The β-Peptide Hairpin in Solution: Conformational Study of a β-Hexapeptide in Methanol by NMR Spectroscopy and MD Simulation

Karl Gademann

The structural and thermodn. properties of a 6-residue β-peptide I that was designed to form a hairpin conformation have been studied by NMR spectroscopy and mol. dynamics simulation in methanol soln. The predicted hairpin would be characterized by a 10-me ...

2001

Pseudoprolines (Psi Pro) in drug design: Direct insertion of Psi Pro systems into cyclosporin C

The insertion of acetals that exhibit variable structural features into complex peptides such as cyclosporin C (CsC) results in oxazolidine derivatives (pseudoprolines, Psi Pro) of tailored physico-chemical and biological properties. N,O-Acetalation of the ...

2000

Synthesis of β-hexa- and β-heptapeptides containing novel β2,3-amino acids with two serine or two cysteine side chains - CD- and NMR-spectroscopic evidence for 314-helical secondary structures in water

Karl Gademann

Two representatives of a new type of beta-amino acids, carrying two functionalized side chains, one in the 2- and one in the 3-position, have been prepd. stereoselectively: a beta-Ser deriv. with an addnl. CH2OH group in the 2-position, for beta-peptides w ...

2000

Influence of cis-trans isomerisation on pentapeptide cyclisation

Cyclisation reactions on pentapeptides containing the turn promoting residues Gly and Pro are investigated. Although the cyclisation reaction is fast, solvent-dependent mixtures of cyclic penta- and decapeptides are observed. NMR studies suggest a strong d ...

1999

Pseudo-prolines in cyclic peptides: Conformational stabilisation of cyclo[Pro-Thr(Psi(Me,Me)Pro)-Pro]

Linear peptide H-Pro-Thr(Psi(Me,Me)pro)-Pro-OH containing a preformed cis-Pro-Thr(Psi(Me,Me)pro) tertiary amide bond cyclises instantaneously and free of formation of oligomeric structures to the cyclic tripeptide cyclo-[Pro-Thr(Psi(Me,Me)pro)-Pro]. Even a ...

1999

Pleated sheets and turns of β-peptides with proteinogenic side chains

Karl Gademann

The authors have prepd. beta-peptides I and II which contg. unlike-beta2,3-amino acids. The structures of beta-peptides I (prepd. in soln.) and II (prepd. on solid-phase) are reported. ...

1999

Total synthesis and conformational studies of hapalosin, N-desmethylhapalosin and 8-deoxyhapalosin

Jieping Zhu

Hapalosin I (R1 = Me, R2 = OH), a 12-membered cyclic depsipeptide possessing MDR-reversing activity, and its analogs, N-desmethylhapalosin I (R1 = H, R2 = OH) and 8-deoxyhapalosin I (R1 = Me, R2 = H), have been synthesized using macrolactamization as an im ...

1999

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