The synthesis of an 11 membered ring bis-lactam, a system which is designed as a conformationally restricted mimetic of type I and type II beta-turns is described. Computer assisted molecular modeling was used to compare the predicted low energy conformers of the turn mimetic with idealized type I a
Methodology for the synthesis of mimetics of peptide β-turns
✍ Scribed by Michael Kahn; Barbara Chen
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 183 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
This letter describes a scenario which provides for the stereospecific intro uction of both the amino and carboxyl termini portion of a designed B-turn mimetic. Peptides and proteins are ubiquitously distributed in nature, and play critical roles in the regulation of virtually all biological processes.
📜 SIMILAR VOLUMES
A dipeptide analog b-turn mimetic with fixed configuration at a-carbons of two amino acid residues in structure type b-turn has been synthesized starting from L-phenilalanine and L-cysteine in short steps.
## Abstract For Abstract see ChemInform Abstract in Full Text.
and L-cysteine form the thiazolidine lactam 2a in a stereoselective and quantitative reaction. Condensation of 5-azido-5-deoxy-D-glucurono-3,6-1actone (lb) with L-cysteine methyl ester followed by the reduction of the azido group yields the rigid [3-tum mimetic 2d in a minimum of reaction steps.