Regioselective alkanoylation of cyclodextrins

  • Donghong Yu
  • Kim Steffensen
  • Jesper Tranholm
  • Anne Louise Nielsen
  • Reinhard Wimmer
  • Kim Lambertsen Larsen
Original Article
First Online:
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Abstract

The regioselective transesterification of native α- and β-Cyclodextrins (CDs) with vinyl acetate and vinyl laurate is presented in this paper. The reactions were carried out in dimethyl sulfoxide by using low molecular weight salts (Na2HPO4 and NaCl, respectively). MALDI-TOF mass spectrometry and NMR analysis were applied to investigate the chemical structure and the degree of the modification of the final products. Results show that these salts catalyze regioselective transesterification between β-CDs and vinyl laurate aiming for the secondary C-2 hydroxyl group. The synthesis and separation of β-CD-laurate derivatives leads to a mixture of mono-2-O-dodecanoyl-β-CD and native β-CDs. Unreacted β-CDs could be selectively removed enzymatically by cyclodextrin glucosyl-transferase (CGTase) and β-amylase.

Keywords

Acetylation Alkanoylation Cyclodextrins Chemical modification Dodecanoylation Regioselectivity 

Abbreviations

AGU

Anhydroglucopyranose unit

CCA

Cyano-4-hydroxycinnamic acid

CD

Cyclodextrin

CGTase

Cyclodextrin glucosyl transferase

DMSO

Dimethyl sulfoxide

FENC

Fast evaporating nitro-cellulose

FT-IR

Fourier transform infrared spectroscopy

HSQC

Heteronuclear single quantum coherence

MALDI-TOF MS

Matrix assisted laser desorption/ionisation time of flight mass spectrometry

NMR

Nuclear magnetic resonance

TFA

Trifluoroacetic acid

TLC

Thin layer chromatography

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • Donghong Yu
    • 1
  • Kim Steffensen
    • 1
  • Jesper Tranholm
    • 1
  • Anne Louise Nielsen
    • 1
  • Reinhard Wimmer
    • 1
  • Kim Lambertsen Larsen
    • 1
  1. 1.Department of Biotechnology, Chemistry and Environmental EngineeringAalborg UniversityAalborgDenmark

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