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Tetrahydrofuran-Based Amino Acids as Library Scaffolds

Edwards, Alison A., Ichihara, Osamu, Murfin, Stephen, Wilkes, Robin, Whittaker, Mark, Watkin, David J., Fleet, George W.J. (2004) Tetrahydrofuran-Based Amino Acids as Library Scaffolds. Journal of Combinatorial Chemistry, 6 (2). pp. 230-238. ISSN 1520-4766. (doi:10.1021/cc034054r) (Access to this publication is currently restricted. You may be able to access a copy if URLs are provided)

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Abstract

A furanose sugar amino acid (SAA) has been utilized as a library scaffold for the first time. Two furanose SAA scaffolds were examined to illustrate their potential for derivatization. The resulting 99-member library contained three orthogonal points of diversification that allowed easy access to ethers and carbamates from a hydroxyl moiety, a range of ureas from an azide (via an amine), and a range of amides from a methyl ester. The novel amide formation (by displacement of the methoxide from the methyl ester moiety) was achieved in good yield and purity with high structural confidence. Full characterization of several library intermediates (including a crystal structure) was obtained. The library was submitted for antibacterial screening.

Item Type: Article
DOI/Identification number: 10.1021/cc034054r
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Faculties > Sciences > Medway School of Pharmacy
Depositing User: Alison Edwards
Date Deposited: 28 May 2009 14:31 UTC
Last Modified: 28 May 2019 13:40 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/4885 (The current URI for this page, for reference purposes)
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