Sugar Functionalization of Silks with Pathway-Controlled Substitution and Properties

Jugal Kishore Sahoo, Onur Hasturk, Jaewon Choi, Maria M. Montero, Marc L. Descoteaux, Isabel A. Laubach, David L. Kaplan

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Silk biomaterials are important for applications in biomedical fields due to their outstanding mechanical properties, biocompatibility, and tunable biodegradation. Chemical functionalization of silk by various chemistries can be leveraged to enhance and tune these features and enable the expansion of silk-based biomaterials into additional fields. Sugars are particularly relevant for intracellular communication, signal transduction events, as well as in hydrated extracellular matrices such as in cartilage, vitreous, and brain tissues. Multiple reaction pathways are demonstrated (carboxylation of serines followed by carbodiimide coupling with glucosamine, carboxylation of tyrosines followed by carbodiimide coupling with glucosamine; direct carbodiimide coupling of the inherent carboxylic acids of silk (aspartic and glutamic acid) with glucosamine) for the covalent conjugation of glucosamine onto silk with characterization by proton nuclear magnetic resonance (1H-NMR), liquid chromatography tandem mass spectroscopy (LC-MS), water contact angle (WCA), and Fourier transform infrared (FTIR) spectroscopy. The results indicate that different pathways substitute different amounts of glucosamine onto silk chains, with control over resulting material properties, including hydrophobicity/hydrophilicity and biological responses. The aqueous processability of these conjugates into functional material formats (films, sponges) is assessed. These new classes of bio-inspired materials can lead to multifunctional biomaterials for potential applications in different fields of biomedical engineering.

Original languageEnglish
Article number2100388
JournalAdvanced Biology
Volume5
Issue number7
DOIs
StatePublished - Jul 2021

Keywords

  • biomaterials
  • pathways
  • silk chemistry
  • sugars
  • surface functionalization

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