Oxazolopiperidin-2-ones as Type II‘ β-Turn Mimetics: Synthesis and Conformational Analysis
- 21 September 2000
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (21) , 6992-6999
- https://doi.org/10.1021/jo000416v
Abstract
We describe a straightforward synthesis of 9-substituted 3-aminooxazolidinopiperidin-2-ones 4. Some derivatives were prepared for use in peptide synthesis as rigidified surrogates of the Ala-Pro dipeptide. Analysis of the amide derivatives 14 by NMR experiments and molecular mechanics/dynamics calculations shows that the major isomer 14a has a stronger propensity than the minor isomer 14b to adopt β-turn conformations, and the calculations indicate that in water 14a adopts a stable βII‘ turn conformation.Keywords
This publication has 12 references indexed in Scilit:
- Synthesis of constrained bicyclic dipeptide mimeticsTetrahedron Letters, 1997
- Aza‐peptides. III. Experimental structural analysis of aza‐alanme and aza‐asparagine‐containing peptidesChemical Biology & Drug Design, 1997
- Peptide models 6. New .beta.-turn conformations from ab initio calculations confirmed by x-ray data of proteinsJournal of the American Chemical Society, 1993
- Validation of the general purpose QUANTA ®3.2/CHARMm® force fieldJournal of Computational Chemistry, 1992
- Synthesis of a highly stable iron porphyrin coordinated by alkylthiolate anion as a model for cytochrome P-450 and its catalytic activity in oxygen-oxygen bond cleavageJournal of the American Chemical Society, 1990
- Comparison of simple potential functions for simulating liquid waterThe Journal of Chemical Physics, 1983
- CHARMM: A program for macromolecular energy, minimization, and dynamics calculationsJournal of Computational Chemistry, 1983
- 1,4-Dialkylgermabenzole - Erzeugung und Nachweis in der GasphaseAngewandte Chemie International Edition in English, 1982
- The novel crystal and molecular structure of bis[bis(2-pyridyl) disulfide]copper(I) perchlorateJournal of the American Chemical Society, 1976
- Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three linked peptide unitsBiopolymers, 1968