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Feast GC, Lepitre T, Mulet X, et al. The search for new amphiphiles: synthesis of a modular, high-throughput library. Beilstein J Org Chem. 2014;10:1578-88doi: 10.3762/bjoc.10.163.
Feast, G. C., Lepitre, T., Mulet, X., Conn, C. E., Hutt, O. E., Savage, G. P., & Drummond, C. J. (2014). The search for new amphiphiles: synthesis of a modular, high-throughput library. Beilstein journal of organic chemistry, 101578-88. https://doi.org/10.3762/bjoc.10.163
Feast, George C, et al. "The search for new amphiphiles: synthesis of a modular, high-throughput library." Beilstein journal of organic chemistry vol. 10 (2014): 1578-88. doi: https://doi.org/10.3762/bjoc.10.163
Feast GC, Lepitre T, Mulet X, Conn CE, Hutt OE, Savage GP, Drummond CJ. The search for new amphiphiles: synthesis of a modular, high-throughput library. Beilstein J Org Chem. 2014 Jul 10;10:1578-88. doi: 10.3762/bjoc.10.163. eCollection 2014. PMID: 25161714; PMCID: PMC4142986.
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Beilstein J Org Chem. 2014 Jul 10;10:1578-88. doi: 10.3762/bjoc.10.163. eCollection 2014.

The search for new amphiphiles: synthesis of a modular, high-throughput library.

Beilstein journal of organic chemistry

George C Feast, Thomas Lepitre, Xavier Mulet, Charlotte E Conn, Oliver E Hutt, G Paul Savage, Calum J Drummond

Affiliations

  1. CSIRO Materials Science and Engineering, Bag 10, Clayton South MDC, VIC 3169, Australia.
  2. CSIRO Materials Science and Engineering, Bag 10, Clayton South MDC, VIC 3169, Australia ; School of Applied Sciences, College of Science, Engineering and Health, RMIT University, GPO Box 2476, Melbourne, VIC 3001, Australia.

PMID: 25161714 PMCID: PMC4142986 DOI: 10.3762/bjoc.10.163

Abstract

Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the copper-catalysed azide-alkyne cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and anomeric linkages. A library of 80 amphiphiles was subsequently produced, using a 24-vial array, with the majority formed in very good to excellent yields. A preliminary assessment of the liquid-crystalline phase behaviour is also presented.

Keywords: amphiphiles; carbohydrates; click chemistry; high throughput; library synthesis

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