Synthesis and aggregation behaviour of single-chain, 1,32-alkyl branched bis(phosphocholines): effect of lateral chain length

文献情報

出版日 2018-03-19

DOI 10.1039/C8OB00424B

インパクトファクター 3.876

著者

K. Gruhle, S. Müller, A. Meister, S. Drescher

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要旨

Three novel single-chain bis(phosphocholines) bearing two lateral alkyl chains of variable length next to the headgroup have been synthesized as model lipids for naturally occurring archaeal membrane lipids. The synthesis was realized using the Cu-catalyzed Grignard bis-coupling reaction of a primary bromide as a side part and a 1,ω-dibromide as a centre part. We could show that the aggregation behaviour of the resulting bolalipids strongly depends on the length of the lateral alkyl chain: the C3-branched bolalipid self-assembles into lamellar sheets, whereas the C6- and C9-analogues form nanofibres. The lamella-forming bolalipids could be used in the future to prepare stable and tailored liposomes for oral drug delivery.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Synthesis and aggregation behaviour of single-chain, 1,32-alkyl branched bis(phosphocholines): effect of lateral chain length

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