Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)

Tools

McGurk, Philip, Chang, Grace X., Lowary, Todd L., McNeil, Michael and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2001) Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). Tetrahedron Letters, 42 (11). pp. 2231-2234. ISSN 0040-4039

Full text not available from this repository. (Request a copy)

Abstract

The stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.

Item Type: Article
Additional Information: Funding Information: This work was supported by US NIH/NIAID AIDS-FIRCA grant R03 TW00938-01 and NIH grant AI 33706, the UK BBSRC (studentship to P.McG.) and the Ohio State University. We thank the EPSRC Mass Spectrometry Service at the University of Wales, Swansea for invaluable support.
Uncontrolled Keywords: 2,5-anhydro-d-mannitol,cell wall biosynthesis,d-arabinose,mycobacteria,phosphonophosphate,biochemistry,drug discovery,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School: Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 10 Sep 2024 12:30
Last Modified: 25 Sep 2024 18:08
URI: https://ueaeprints.uea.ac.uk/id/eprint/96662
DOI: 10.1016/S0040-4039(01)00118-6

Actions (login required)

View Item View Item