ChemInform Abstract: Conformational Control by Thiazole and Oxazoline Rings in Cyclic Octapeptides of Marine Origin. Novel Macrocyclic Chair and Boat Conformations.
✍ Scribed by G. ABBENANTE; D. P. FAIRLIE; L. R. GAHAN; G. R. HANSON; G. K. PIERENS; A. L. VAN DEN BRENK
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 29 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Conformational Control by Thiazole and Oxazoline Rings in Cyclic
Octapeptides of Marine Origin. Novel Macrocyclic Chair and Boat Conformations.
-The two common amino acid building blocks cystein and threonine in (II) act as conformational ring constraints to regulate the threedimensional structures and reactivities of marine macrocycles. Conversion of the cystein residues to 5-membered thiazole rings leads to the formation of a novel pseudochair conformation in (I) with restricting the conformational flexibility of (I). Additional conversion of the threonine side chains to 5-membered oxazoline rings creates unusual shapes capable to capture organic or metal ion guests.