Chakraborty, Tushar K. ; Ghosh, Animesh ; Nagaraj, R. ; Ravi Sankar, A. ; Kunwar, Ajit C. (2001) Synthesis and conformational studies of peptidomimetics containing a carbocyclic 1,3-diacid Tetrahedron, 57 (44). pp. 9169-9175. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)00921-8
Abstract
A rigid carbocyclic scaffold comprising of an all-cis 4,5-dihydroxy-1,3-cyclopentanedicarboxylic acid is developed. Attachment of peptide strands to the carboxylic groups of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by circular dichroism and NMR studies revealed that these molecules adopt a unique folded structure in nonpolar solvent involving intramolecular hydrogen bonding between PheNH of one strand and LeuC=O (in 2) or GlyC=O (in 3) of the other strand. This structure is very different from the structures observed earlier in their sugar counterparts (1). The paper describes in detail the synthesis and structural studies of compounds 2 and 3.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Peptide Mimetics; Hydrogen Bonding; Conformation; NMR; Diels-Alder Reactions |
| ID Code: | 20603 |
| Deposited On: | 20 Nov 2010 13:53 |
| Last Modified: | 22 May 2011 15:48 |
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