Tetrahydrofuran-Based Amino Acids as Library Scaffolds

Edwards, Alison A. and Ichihara, Osamu and Murfin, Stephen and Wilkes, Robin and Whittaker, Mark and Watkin, David J. and Fleet, George W.J. (2004) Tetrahydrofuran-Based Amino Acids as Library Scaffolds. Journal of Combinatorial Chemistry, 6 (2). pp. 230-238. ISSN 1520-4766 . (Access to this publication is restricted)

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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
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > Medway School of Pharmacy
Depositing User: Alison Edwards
Date Deposited: 28 May 2009 14:31
Last Modified: 28 May 2012 10:46
Resource URI: http://kar.kent.ac.uk/id/eprint/4885 (The current URI for this page, for reference purposes)
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