Design, Synthesis, and Characterization of Tyrosinophanes, a Novel Family of Aromatic-Bridged Tyrosine-Based Cyclodepsipeptides

Ranganathan, Darshan and Thomas, A and Haridas, V and Kurur, S and Madhusudanan, KP and Roy, Raja and Kunwar, AC and Sarma, AVS and Vairamani, M and Sarma, KD (1999) Design, Synthesis, and Characterization of Tyrosinophanes, a Novel Family of Aromatic-Bridged Tyrosine-Based Cyclodepsipeptides. In: Journal of Organic Chemistry, 64 (10). pp. 3620-3629.

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Abstract

A simple two-step design strategy has been developed for the synthesis of a large variety of a new class of tyrosine-based aromatic (Ph or Pyr) bridged cyclodepsipeptides (tyrosinophanes). The design is flexible with respect to the size of the ring and the nature of the bridging unit and permits the incorporation of a variety of amino acid residues inside or outside or both inside and outside the ring as illustrated here with the preparation of tyrosine-based macrocycles with aromatic (Ph or Pyr), cage-like alicyclic (adamantane) or simple polymethylene bridging units in ring sizes varying from 26-membered to 78-membered and containing leucine residues as part of the ring or. as pendants on the exterior or both inside and outside the macrocyclic ring. H-1 NMR, FT-IR, and CD studies have indicated open-ring structures for these macrocycles. A noteworthy feature of the strategy is the formation of the 1 + 1 + 1 + 1 catenane arising from the interlocking of sebacoyl-bridged tyrosine rings. The potential of tyrosinophanes to serve as simple aromatic hosts in the study of Jr-cation type interactions was illustrated with Pyr-bridged macrocycles (6b-8b) using N-methylacridinium hexafluorophosphate as the pyridinium guest. The K-assoc value with 6b was found to be 8.95 x 10(3) M-1.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	Copyright of this article belongs to American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	06 Mar 2009 08:31
Last Modified:	19 Sep 2010 05:01
URI:	http://eprints.iisc.ac.in/id/eprint/18384

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