Microwave-assisted synthesis and characterization of hydrophilically functionalized polygalacturonic acid

Zarif Farhana Mohd Aris; Ryan M Bouldin; Margery G H Pelletier; Peter Gaines; Bridgette Budhlall; Ramaswamy Nagarajan

doi:10.1016/j.carbpol.2016.08.070

Microwave-assisted synthesis and characterization of hydrophilically functionalized polygalacturonic acid

Carbohydr Polym. 2017 Jan 2:155:432-439. doi: 10.1016/j.carbpol.2016.08.070. Epub 2016 Aug 22.

Authors

Zarif Farhana Mohd Aris¹, Ryan M Bouldin², Margery G H Pelletier³, Peter Gaines³, Bridgette Budhlall⁴, Ramaswamy Nagarajan⁵

Affiliations

¹ Renewable Materials Laboratory, Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA, 01854, USA; Department of Plastics Engineering, University of Massachusetts Lowell, Lowell, MA, 01854, USA.
² Department of Natural and Applied Sciences, Bentley University, Waltham, MA, 02452, USA.
³ Department of Biological Science, University of Massachusetts Lowell, Lowell, MA, 01854, USA.
⁴ Department of Plastics Engineering, University of Massachusetts Lowell, Lowell, MA, 01854, USA.
⁵ Renewable Materials Laboratory, Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA, 01854, USA; Department of Plastics Engineering, University of Massachusetts Lowell, Lowell, MA, 01854, USA. Electronic address: Ramaswamy_nagarajan@uml.edu.

PMID: 27702532
DOI: 10.1016/j.carbpol.2016.08.070

Abstract

Microwave-assisted synthesis of a new class of polymeric surfactants based on polygalacturonic acid (PGA) is presented. PGA is water-insoluble and not surface-active under normal conditions. Single-step hydrophilic modification of PGA with taurine (2-aminoethane sulfonic acid) renders it surface-active. The modification can be carried out either using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCl) as a coupling agent or using microwave irradiation without a catalyst. Microwave irradiation significantly shortens reaction times and eliminates the need for a coupling agent. In all cases, functionalization was confirmed using ¹H NMR, FTIR spectroscopy and elemental analysis. PGA-SO₃ exhibits surface-active properties comparable to commercial surfactants, Triton X-100 and sodium lauryl sulfate. Detailed cytotoxicity evaluation performed using human dermal fibroblast (HDF) and human leukemic (HL-60) cell lines indicate that PGA-SO₃ is not toxic even at 20 fold higher concentrations. These polymeric surfactants synthesized from PGA with no demonstrable cytotoxicity have the potential for serving as 'greener' alternatives to common petrochemical-based surfactants.

Keywords: Detergency; Macromolecule; Microwave-catalyzed; Pectic acid; Polysaccharide-based surfactant.