MilliporeSigma

Thiols

Biphenyl-4-thiol Bottle

Thiols, also known as mercaptans or sulfhydryl, are organic compounds featuring a sulfur atom bonded to a hydrogen atom (-SH group). Thiols are used in various applications, serving as additives for controlling odors, functioning as reducing agents in chemical reactions, and acting as building blocks in organic synthesis. Some thiols also play important roles in biological processes, such as enzyme reactions and cellular signaling.

Thiols as Heterocyclic Building Blocks

Heterocyclic thiols contain a heterocyclic ring and are used as building blocks in the synthesis of pharmaceutical compounds, contribute to the development of pesticides and herbicides, act as fundamental components in synthesizing various organic compounds, and function as analytical reagents and standards for detecting and quantifying specific substances in analytical chemistry.

Purpald®

Purpald® reagent, also known as 4-amino-3-hydrazino-5-mercapto-1,2,4-triazole, is a chemical compound used as a reagent for detecting and quantifying aldehydes and ketones. It is commonly used in analytical chemistry and organic synthesis.

Thiols as Biomedical Polymers

Thiols exhibit unique and beneficial properties when used in biomedical polymers contributing to enhanced biodegradability, biocompatibility, and specificity in chemical reactivity.

Thiols can be used in various applications, such as forming hydrogels, which are three-dimensional networks of crosslinked polymers. Hydrogels can mimic the natural environment of tissues and cells, making them suitable for drug delivery, tissue engineering, and wound healing. Thiols are also used in polymer modification, act as drug delivery systems, and serve as biomedical adhesives in the development of tissue adhesives and hemostatic agents.

Thiolated gelatin

Thiols can be cross-linked through the formation of covalent bonds, resulting in highly crosslinked structures, such as hydrogels. Thiol-modified gelatin, for example, can be used to create hydrogels with multifunctional norbornene or allyl crosslinkers via thiol-ene click or Michael-addition reactions.

This unique ability makes thiolated gelatin a versatile material, serving as a bioink or matrix in 3D bioprinting. Through a thiol-ene reaction, it facilitates covalent crosslinking, providing essential mechanical stability to the printed tissue constructs.

Thiols in Amino acids, Resins and Reagents for Peptide Synthesis

Thiols play important roles in amino acids, resins, and reagents used in peptide synthesis.

Thiols in Amino Acids

Cysteine is an amino acid that contains a thiol group, capable of forming disulfide bonds with other cysteine residues. Disulfide bonds play a crucial role in stabilizing protein structures and can be strategically utilized in peptide synthesis to introduce structural constraints or facilitate protein folding.

Thiols in Resins

Thiols are commonly used in solid-phase peptide synthesis (SPPS) to immobilize the growing peptide chain onto a solid support. Merrifield resin, one of the most widely used resins in SPPS, contains thiol groups that can react with carboxylic acid, forming an amide bond.

Thiols as Reagents for Peptide Synthesis

In peptide synthesis, thiol-containing reagents are utilized for various purposes. Dithiothreitol (DTT), a reducing agent that breaks disulfide bonds, is used in the cleavage and deprotection steps of peptide synthesis, facilitating the release of the synthesized peptide from the resin. Other thiol-based reagents, such as 2-mercaptoethanol or tris(2-carboxyethyl) phosphine, can also be used as reducing agents or stabilizers during peptide synthesis.



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