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) (KAR id:4885)
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| Official URL: http://dx.doi.org/10.1021/cc034054r |
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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: | Divisions > Division of Natural Sciences > Medway School of Pharmacy |
| Funders: |
Biotechnology and Biological Sciences Research Council (https://ror.org/00cwqg982)
Evotec (United Kingdom) (https://ror.org/04qvy9k41) |
| Depositing User: | Alison Edwards |
| Date Deposited: | 28 May 2009 14:31 UTC |
| Last Modified: | 05 Nov 2024 09:36 UTC |
| Resource URI: | https://kar.kent.ac.uk/id/eprint/4885 (The current URI for this page, for reference purposes) |
University of Kent Author Information
Edwards, Alison A..
| Creator's ORCID: |
 https://orcid.org/0000-0002-4637-9373
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