Carbohydrate-derived conformationally restricted bicyclic dipeptides as potential hetero foldamer building blocks

TitleCarbohydrate-derived conformationally restricted bicyclic dipeptides as potential hetero foldamer building blocks
Publication TypeJournal Article
Year of Publication2012
AuthorsRamesh, VVE, Puranik, VG, Sanjayan, GJ
JournalTetrahedron-Asymmetry
Volume23
Issue18-19
Pagination1400-1404
Date PublishedOCT
ISSN0957-4166
Abstract

Starting from carbohydrate precursors, hetero foldamer building blocks featuring diverse amino acid side chains and stereochemistry have been accessed via a multi-step synthetic protocol. These conformationally restricted bicyclic dipeptide building blocks are characterized by a constrained beta-lactam ring fused with a pyrrolidine ring carrying a hydroxyethylamine isostere (HEA) on the backbone. These building blocks offer the possibility of developing foldamers with interesting structural architectures, conspicuously different from those classically observed. Furthermore, such hetero-building blocks have the potential to augment the conformational space available for foldamer design with diverse backbone conformations and structural architectures. (C) 2012 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetasy.2012.08.007
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.115

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry