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Efficient synthesis of methanesulphonate-derived lipid chains for attachment of proteins to lipid membranes
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Hicks, Matthew R., Rullay, Atvinder K., Pedrido, Rosa, Crout, D. H. G. and Pinheiro, Teresa J. T. (2008) Efficient synthesis of methanesulphonate-derived lipid chains for attachment of proteins to lipid membranes. Synthetic Communications, Volume 38 (Number 21). pp. 3726-3750. doi:10.1080/00397910802213794 ISSN 0039-7911.
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Official URL: http://dx.doi.org/10.1080/00397910802213794
Abstract
We have developed an easy and flexible synthetic methodology to obtain lipid chains containing methanothiosulfonate terminal groups with the aim to attach them to natural proteins as functional groups. There are many proteins found in nature that are modified by lipids, and this is a key part of their function. For example, the prion protein is attached to the plasma membrane via a glycosylphosphatidylinositol (GPI) anchor, and this protein is thought to be the causative agent in diseases such as bovine spongiform encephalopathy (BSE; mad cow disease) and the human equivalent Creutzfeldt-Jakob disease. However, production of large amounts of protein in bacteria results in proteins that lack these lipid modifications. The lipid chains containing methanothiosulfonate terminal groups that we have synthesized here can be attached to these proteins through the thiol contained in the side chain of the cysteine residue, which can be incorporated into the protein sequence at the desired position.
| Item Type: | Journal Article | ||||
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| Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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| Divisions: | Faculty of Science, Engineering and Medicine > Science > Life Sciences (2010- ) > Biological Sciences ( -2010) Faculty of Science, Engineering and Medicine > Science > Chemistry |
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| Library of Congress Subject Headings (LCSH): | Glycolipids, Prions, Lipids -- Synthesis, Methanesulfonates | ||||
| Journal or Publication Title: | Synthetic Communications | ||||
| Publisher: | Taylor & Francis Inc. | ||||
| ISSN: | 0039-7911 | ||||
| Official Date: | 2008 | ||||
| Dates: |
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| Volume: | Volume 38 | ||||
| Number: | Number 21 | ||||
| Number of Pages: | 25 | ||||
| Page Range: | pp. 3726-3750 | ||||
| DOI: | 10.1080/00397910802213794 | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access | ||||
| Funder: | Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC), Galicia (Spain : Region). Xunta | ||||
| Grant number: | 88/BS51647 (BBSRC) |
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