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Angew Chem Int Ed Engl. 2014 Dec 15;53(51):14102-5. doi: 10.1002/anie.201408538. Epub 2014 Oct 24.

In situ vesicle formation by native chemical ligation.

Author information

1
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, Urey Hall 4120, La Jolla, CA 92093 (USA) http://devarajgroup.ucsd.edu.

Abstract

Phospholipid vesicles are of intense fundamental and practical interest, yet methods for their de novo generation from reactive precursors are limited. A non-enzymatic and chemoselective method to spontaneously generate phospholipid membranes from water-soluble starting materials would be a powerful tool for generating vesicles and studying lipid membranes. Here we describe the use of native chemical ligation (NCL) to rapidly prepare phospholipids spontaneously from thioesters. While NCL is one of the most popular tools for synthesizing proteins and nucleic acids, to our knowledge this is the first example of using NCL to generate phospholipids de novo. The lipids are capable of in situ synthesis and self-assembly into vesicles that can grow to several microns in diameter. The selectivity of the NCL reaction makes in situ membrane formation compatible with biological materials such as proteins. This work expands the application of NCL to the formation of phospholipid membranes.

KEYWORDS:

membranes; native chemical ligation; phospholipids; self-assembly; synthetic biology

PMID:
25346090
PMCID:
PMC4418804
DOI:
10.1002/anie.201408538
[Indexed for MEDLINE]
Free PMC Article

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