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Brown, Jillian R., Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275, Barker, Adam, Guy, Mark, Grewal, Ravinder, Khoo, Kay Hooi, Brennan, Patrick J., Besra, Gurdyal S. and Chatterjee, Delphi
(2001)
Synthetic mannosides act as acceptors for mycobacterial α1-6 mannosyltransferase.
Bioorganic and Medicinal Chemistry, 9 (4).
pp. 815-824.
ISSN 0968-0896
Abstract
A series of synthetic mannosides was screened in a cell-free system for their ability to act as acceptor substrates for mycobacterial mannosyltransferases. Evaluation of these compounds demonstrated the incorporation of [14C]Man from GDP-[14C]Man into a radiolabeled organic-fraction and analysis by thin layer chromatography and autoradiography revealed the formationof two radiolabeled products. Each synthetic acceptor was capable of accepting one or two mannose residues, resulting in a major and a minor mannosylated product. Both products from each acceptor were isolated and their mass was confirmed by fast-atom bombardment-mass spectrometry FABMS). Characterization of each mannosylated product by exo-glycosidase digestion, acetolysis and linkage analysis by gas chromatography-mass spectrometry of partially per-O-methylated alditols, revealed only α1-6-linked products. In addition, the antibiotic amphomycin selectively inhibited the formation of mannosylated products suggesting polyprenolmonophosphate-mannose C35/50-P-Man) was the immediate mannose donor in all mannosylation reactions observed. The ability of synthetic disaccharides to act as acceptor substrates in this system, is most likely due to the action of a mycobacterial polyprenol-P-Man:mannan α1-6 mannosyltransferase involved in the biosynthesis of linear α1-6-linked lipomannan.
| Item Type: | Article |
|---|---|
| Additional Information: | Funding Information: We thank Dr Mike McNeil for assistance with GC and GC–MS and Mr Don Dick for running ES–MS. This work was supported by NIH NIAID grants AI 37139, UI AI 40972 and AI 38087. GSB is supported by a Lister Institute-Jenner Research Fellowship. GSB would like to thank the Wellcome Trust for funding. JRB would like to thank the Wellcome Trust for a Travel Grant. |
| Uncontrolled Keywords: | biochemistry,molecular medicine,molecular biology,pharmaceutical science,drug discovery,clinical biochemistry,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: | 11 Sep 2024 09:30 |
| Last Modified: | 25 Sep 2024 18:08 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/96683 |
| DOI: | 10.1016/S0968-0896(00)00300-X |
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