Synthesis and characterization of carbohydrate-based biosurfactant mimetics

Kaitlynn A Sockett; Madeline Loffredo; Jenny Korunes-Miller; Maria Varghese; Mark W Grinstaff

doi:10.1016/j.carres.2022.108697

Synthesis and characterization of carbohydrate-based biosurfactant mimetics

Carbohydr Res. 2022 Dec:522:108697. doi: 10.1016/j.carres.2022.108697. Epub 2022 Oct 7.

Authors

Kaitlynn A Sockett¹, Madeline Loffredo², Jenny Korunes-Miller³, Maria Varghese⁴, Mark W Grinstaff⁵

Affiliations

¹ Department of Chemistry, Boston University, Boston, MA, 02215, United States.
² Department of Material Science Engineering, Boston University, Boston, MA, 02215, United States.
³ Department of Biomedical Engineering, Boston University, Boston, MA, 02215, United States.
⁴ Department of Chemistry, Boston University, Boston, MA, 02215, United States. Electronic address: mariavar@bu.edu.
⁵ Department of Chemistry, Boston University, Boston, MA, 02215, United States; Department of Material Science Engineering, Boston University, Boston, MA, 02215, United States; Department of Biomedical Engineering, Boston University, Boston, MA, 02215, United States. Electronic address: mgrin@bu.edu.

Abstract

Glycolipid biosurfactants are of interest for various industry sectors. We report the synthesis and characterization of enantiopure poly-amido-saccharides (PASs) containing myristoyl (C14), palmitoyl (C16), or stearoyl (C18) terminal chain lengths as mimetics of glycolipid biosurfactants. These amphiphilic polymers are water soluble, adopt a helical secondary structure, decompose at temperatures greater than 240 °C, are non-cytotoxic, and self-assemble into nanostructures. Polymers containing the shorter hydrophilic chain lengths and the hydrophobic C14 chain exhibit the lowest surface tension among all polymers.

Keywords: Amphiphilic polymers; Fatty acid; Nanoparticles; Poly-amido-saccharide; Polysaccharides; Surfactants.

MeSH terms

Carbohydrates* / chemistry
Glycolipids*
Hydrophobic and Hydrophilic Interactions
Polymers / chemistry
Surface-Active Agents / chemistry

Substances

Carbohydrates
Glycolipids
Polymers
Surface-Active Agents

Grants and funding

R01 HL164650/HL/NHLBI NIH HHS/United States