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Head group-modified sophorolipids: Synthesis of new cationic, zwitterionic, and anionic surfactants

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Journal of Surfactants and Detergents

Abstract

Amino acid-glycolipid conjugates were prepared using carbodiimide-mediated coupling methods. The amino acid units were multifunctional and possessed a para-aminobenzoic acid linker. The glycolipid used was a stearic sophoroside. The aim of preparing these modified sophorolipids was to increase their water solubility as well as to introduce sites at the polar head groups that permitted further chemical derivatization. After acidolytic or hydrogenolytic deprotection of the amino acid N-terminus or side chain, water-soluble compounds were obtained that displayed good surfactant properties. Critical micelle concentration values were clustered in the range of high 10−6 to low 10−5 M, and minimum surface tension values were below 40 mN m−1. Two of the compounds represented more complicated structural classes, namely, gemini and bolaform surfactants.

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Abbreviations

Boc:

butoxycarbonyl

Cbz:

benzyloxycarbonyl

CMC:

critical micelle concentration

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

DMAP:

4-dimethylaminopyridine

DMF:

dimethylformamide

DMSO:

dimethylsulfoxide

EDC:

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

HOBt:

1-hydroxybenzotriazole hydrate

HPLC:

high-performance liquid chromatography

LC-MS:

liquid chromatography-mass spectrometry

Lys(Cbz):

N-ε-benzyloxycarbonyl lysine

NMR:

nuclear magnetic resonance

Paba:

4-aminobenzoic acid

SL:

sophorolipids

THF:

tetrahydrofuran

TLC:

thin-layer chromatography

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Authors and Affiliations

  1. Eastern Regional Research Center, ARS, USDA, 600 East Mermaid Lane, 19038, Wyndmoor, PA

    Jonathan A. Zerkowski, Daniel K. Y. Solaiman, Richard D. Ashby & Thomas A. Foglia

Authors
  1. Jonathan A. Zerkowski
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  2. Daniel K. Y. Solaiman
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  3. Richard D. Ashby
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  4. Thomas A. Foglia
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Correspondence to Jonathan A. Zerkowski.

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Zerkowski, J.A., Solaiman, D.K.Y., Ashby, R.D. et al. Head group-modified sophorolipids: Synthesis of new cationic, zwitterionic, and anionic surfactants. J Surfact Deterg 9, 57–62 (2006). https://doi.org/10.1007/s11743-006-0375-x

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  • DOI: https://doi.org/10.1007/s11743-006-0375-x

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