Novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry

TitleNovel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry
Publication TypeJournal Article
Year of Publication2006
AuthorsEdwards, AA, Sanjayan, GJ, Hachisu, S, Tranter, GE, Fleet, GWJ
JournalTetrahedron
Volume62
Issue33
Pagination7718-7725
Date PublishedAUG
Type of ArticleArticle
ISSN0040-4020
KeywordsFoldamers, gamma amino acids, Peptidomimetics, sugar amino acids
Abstract

Two tetrahydrofuran-based y-amino acids [2,4-cis and 2,4-trans] were subjected to iterative peptide-coupling procedures to afford dimeric, tetrameric and hexameric carbopeptoids in good yield. These homooligomers were prepared for secondary structural study-to ascertain the conformational preference inherent in the monomer units. The L-xylo oligomers were protected with triethylsilyl ethers to increase the range of solvents suitable for structural investigation. Initial secondary structure data indicate the presence of hydrogen-bonded conformations in the L-ribo series. (c) 2006 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2006.05.067
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.645

Divison category: 
Organic Chemistry