Recent advances in S–S bond formation

Mandal, Bablee; Basu, Basudeb

doi:10.1039/c3ra45997g

Cited by 185 publications

(86 citation statements)

References 141 publications

(67 reference statements)

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“…[1][2][3][4][5][6][7][8] Owing to the increasing importance of the disulfides (disulfanes) in chemistry [9][10][11][12][13][14] and biology, [15][16][17] synthetic approaches for their preparation have been extensively studied. [18][19][20][21][22] According to the literature, disulfides can be obtained directly from *Corresponding author. Email: khalili@shirazu.ac.ir thiocyanates, [23][24][25] alcohols [26][27][28] and sulfonyl chlorides.…”

Section: Introductionmentioning

confidence: 99%

4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

Khalili

Iranpoor

Firouzabadi

2015

Journal of Sulfur Chemistry

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Heterocyclic azo compounds, prepared from corresponding amines in one step, are used as effective oxidants for the conversion of thiols into symmetrical disulfides in high yields. Among the studied azo compounds, 4,4 -azopyridine was found to be very efficient for the odorless conversion of alkyl halides into disulfides in the presence of thiourea. An attractive feature of this azo compound is that its obtained solid side product hydrazine is easily separated by filtration and can be recycled to its azo compound for further use.

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Section: Introductionmentioning

confidence: 99%

4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

Khalili

Iranpoor

Firouzabadi

2015

Journal of Sulfur Chemistry

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“…Thiolated gelatin (GS) was obtained after lyophilization, and the thiol content in GS was determined by Ellman's test. [16,17] The …”

Section: Synthesis Of Thiolated Gelatin (Gs)mentioning

confidence: 99%

Enhanced tissue adhesiveness of injectable gelatin hydrogels through dual catalytic activity of horseradish peroxidase

et al. 2017

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Development of bioadhesives with tunable mechanical strength, high adhesiveness, biocompatibility, and injectability is greatly desirable in all surgeries to replace or complement the sutures and staples. Herein, the dual catalytic activity of horseradish peroxidase is exploited to in situ form the hydroxyphenyl propionic acid-gelatin/thiolated gelatin (GH/GS) adhesive hydrogels including two alternative crosslinks (phenol-phenol and disulfide bonds) with fast gelation (few seconds -several minutes) and improved physicochemical properties. Their elastic moduli increase from 6.7 to 10.3 kPa by adding GS polymer that leads to the better stability of GH/GS hydrogels than GH ones.GH/GS adhesive strength is respectively 6.5-fold and 15.8-fold higher than GH-only and fibrin glue that is due to additional disulfide linkages between hydrogels and tissues. Moreover, in vitro cell study with human dermal fibroblast showed the cell-compatibility of GH/GS hydrogels. Taken together, GH/GS hydrogels can be considered as promising potential adhesive materials for various biomedical applications. K E Y W O R D Sadhesives, biodegradability, gelatin, in situ forming hydrogels, thiomers

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“…Other strategies include reduction the of p ‐nitrobenzyl protecting group ( S ‐pNB) to a p ‐aminobenzyl group ( S ‐pAB) prior to oxidation by I 2 , oxidation of the S ‐ t Bu group by O 2 in a large excess of cysteine and a chaotropic salt and enzymatic cleavage of phenylacetamidomethyl groups ( S ‐Phacm) followed oxidation in the presence of DMSO in aqueous conditions . However, disulfide formation by oxidation allows only the formation of symmetrical disulfides and suffers from drawbacks such as removal of the oxidizing agent, low yield, long reaction time, and the formation of side products …”

Section: Synthesis Of Polypeptidesmentioning

confidence: 99%

Of Thiols and Disulfides: Methods for Chemoselective Formation of Asymmetric Disulfides in Synthetic Peptides and Polymers

Schäfer

Barz

2018

Chemistry A European J

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In protein or peptide chemistry, thiols are frequently chosen as a chemical entity for chemoselective modification reactions. Although it is a well-established methodology to address cysteines and homocysteines in aqueous media to form S-C bonds, possibilities for the chemoselective formation of asymmetric disulfides have been less approached. Focusing on bioreversibility in conjugation chemistry, the formation of disulfide bonds is highly desirable for the attachment of thiol-containing bioactive agents to proteins or in cross-linking reactions, because disulfide bonds can combine stability in blood with degradability inside cells. In this Concept article, recent approaches in the field of activating groups for thiol moieties incorporated in peptide and polymer materials are highlighted. Advantageous combinations of stability during synthesis of the material with high reactivity towards thiols are explored focusing on simplification and prevention of side reactions as well as additional deprotection and activation steps prior to disulfide formation. Moreover, applications of this chemistry are highlighted and future perspectives are envisioned.

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Recent advances in S–S bond formation

Cited by 185 publications

References 141 publications

4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

Enhanced tissue adhesiveness of injectable gelatin hydrogels through dual catalytic activity of horseradish peroxidase

Of Thiols and Disulfides: Methods for Chemoselective Formation of Asymmetric Disulfides in Synthetic Peptides and Polymers

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