Issue 21, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Tetrahydrofuran amino acids: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid

Natasha L. Hungerford,a   Timothy D. W. Claridge,a   Mark P. Watterson,a   Robin T. Aplin,a   Andres Morenoa  and  George W. J. Fleet*a  

* Corresponding authors

a The Dyson Perrins Laboratory, University of Oxford, Oxford Centre for Molecular Sciences, South Parks Road, Oxford, UK

Abstract

The synthesis of a D-allo-5-(azidomethyl)tetrahydrofuran-2-carboxylate as an amino acid precursor (in which the carboxylic acid is cis to the azidomethyl substituent and trans to the diol moiety) is reported from D-ribose. The oligomerisation of this monomer to dimeric, tetrameric and octameric carbopeptoids is described. NMR studies into the solution structures of cyclohexylidene-protected oligomers and of a deprotected tetramer with eight free hydroxy groups are described.

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Article information

DOI
https://doi.org/10.1039/B002996N
Article type
Paper
Submitted
13 Apr 2000
Accepted
14 Aug 2000
First published
19 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3666-3679

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Tetrahydrofuran amino acids: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid

N. L. Hungerford, T. D. W. Claridge, M. P. Watterson, R. T. Aplin, A. Moreno and G. W. J. Fleet, J. Chem. Soc., Perkin Trans. 1, 2000, 3666 DOI: 10.1039/B002996N

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