2023
DOI: 10.1039/d3cc02646a
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Rapid, green disulphide bond formation in water using the corrin dicyanocobinamide

Alyssa Spear,
Oleksandr Orativskyi,
Samantha Tran
et al.

Abstract: Peptide chemists seek rapid methods combined with facile purification when producing disulfide bonds post solid-phase synthesis. Current methods typically require long reaction times of up to two days, can result...

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Cited by 2 publications
(1 citation statement)
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“…3,4 Covalent attachment of maleimide-based cytotoxic payloads to cysteine residues generated from the reduction of native disulfide bonds in monoclonal antibodies (mAbs) is the preferred bioconjugation strategy for most FDA-approved ADCs (A). [5][6][7] While a breadth of chemical and enzymatic methods have been developed for thiol oxidation to disulfides, [8][9][10] the reverse reaction of disulfide reduction to thiols has received very little attention and, to this day, is exclusively achieved using stoichiometric amounts of reducing agents. 11 For example, reducing the internal disulfide bonds in mAbs for bioconjugation in ADCs typically requires stoichiometric reagents such as tris(2-carboxyethyl)phosphine (TCEP) 12,13 or other water-soluble phosphines (Figure 1B).…”
mentioning
confidence: 99%
“…3,4 Covalent attachment of maleimide-based cytotoxic payloads to cysteine residues generated from the reduction of native disulfide bonds in monoclonal antibodies (mAbs) is the preferred bioconjugation strategy for most FDA-approved ADCs (A). [5][6][7] While a breadth of chemical and enzymatic methods have been developed for thiol oxidation to disulfides, [8][9][10] the reverse reaction of disulfide reduction to thiols has received very little attention and, to this day, is exclusively achieved using stoichiometric amounts of reducing agents. 11 For example, reducing the internal disulfide bonds in mAbs for bioconjugation in ADCs typically requires stoichiometric reagents such as tris(2-carboxyethyl)phosphine (TCEP) 12,13 or other water-soluble phosphines (Figure 1B).…”
mentioning
confidence: 99%