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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, David H. 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. 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

Subjects:

Q Science > QD Chemistry
Q Science > QP Physiology

Divisions:

Faculty of Science > Life Sciences (2010- ) > Biological Sciences ( -2010)
Faculty of Science > Chemistry

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:

Date	Event
2008	Published

Volume:

Volume 38

Number:

Number 21

Number of Pages:

Page Range:

pp. 3726-3750

Identification Number:

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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