Journal of Surfactants and Detergents

, Volume 9, Issue 1, pp 57–62

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

  • Jonathan A. Zerkowski
  • Daniel K. Y. Solaiman
  • Richard D. Ashby
  • Thomas A. Foglia
Article

DOI: 10.1007/s11743-006-0375-x

Cite this article as:
Zerkowski, J.A., Solaiman, D.K.Y., Ashby, R.D. et al. J Surfact Deterg (2006) 9: 57. doi:10.1007/s11743-006-0375-x

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.

Key Words

Amino acidsbioconjugateglycolipidsophorolipidsurfactants

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

Copyright information

© AOCS Press 2006

Authors and Affiliations

  • Jonathan A. Zerkowski
    • 1
  • Daniel K. Y. Solaiman
    • 1
  • Richard D. Ashby
    • 1
  • Thomas A. Foglia
    • 1
  1. 1.Eastern Regional Research Center, ARSUSDAWyndmoor