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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Glycosaminoglycans (GAGs), also known as mucopolysaccharides, are long and linear polymers comprising of specific repeating disaccharides - the amino sugar that can be N-acetylglucosamine or N-acetylgalactosamine, and a uronic acid that is usually glucuronic acid or iduronic acid.
GAGS are found in the extracellular matrix of vertebrates, invertebrates, and bacteria. Due to their polar nature they attract water, and serve as excellent lubricants or shock absorbers in an animal body.
Hyaluronic...
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Sulfonated Hyaluronic Acid-Based Polymers and Hydrogels Using Thiol-Ene and Thiol-Michael Reactions.

Ivo Anton Octave Beeren1,2, Pieter Jelle Dijkstra1, Ane Albillos Sanchez1

  • 1Department of Complex Tissue Regeneration, MERLN Institute for Technology-Inspired Regenerative Medicine, Maastricht University, Maastricht, The Netherlands.

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Summary

This study introduces a novel method to add sulfonate groups to hyaluronic acid (HA) for tissue engineering. This approach avoids harsh conditions, enabling the creation of tunable HA-based hydrogels for potential biomedical applications.

Keywords:
carboxylic acid activationhyaluronic acidsulfonated hydrogelssulfonation

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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Tissue Engineering

Background:

  • Non-sulfated polysaccharides like hyaluronic acid (HA) are explored for tissue engineering scaffolds.
  • Mimicking sulfated glycosaminoglycans requires sulfate grafting, but harsh conditions cause degradation.
  • Sulfonates offer a sulfate-like function but haven't been applied to polysaccharides.

Purpose of the Study:

  • To develop a mild, two-step strategy for introducing tunable sulfonate groups onto HA.
  • To create HA-based hydrogels with controlled stiffness and sulfonate content.
  • To establish a versatile method applicable to other polysaccharides.

Main Methods:

  • Grafting norbornene (NB) or maleimide (MAL) onto HA using DMTMM activation.
  • Coupling 3-mercapto-1-propanesulfonate (MPS) via thiol-ene and thiol-Michael additions.
  • Forming hydrogels using poly(ethylene glycol)-di-SH crosslinker with NB-conjugated HA.

Main Results:

  • Tunable sulfonate groups were successfully introduced onto HA without backbone degradation.
  • HA-MAL showed poor crosslinking kinetics, limiting its application.
  • Hydrogels with tunable stiffness and sulfonate density were formed using NB-conjugated HA and MPS.
  • The strategy demonstrated high efficiency and applicability to polysaccharide modification.

Conclusions:

  • A simple, efficient strategy for sulfonate modification of HA was established.
  • This method overcomes limitations of traditional sulfate grafting for tissue engineering.
  • The developed HA-based hydrogels offer tunable properties for biomedical applications.
  • The approach is potentially extendable to other polysaccharides, broadening its impact.