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US 11,560,387 B2Granted
Thermally sensitive protecting groups for cysteine, and manufacture and use thereof
OwnerJohn Frederick Trant, Daniel Meister +5inventors
InventorsJohn Frederick Trant, Daniel Meister, Sarah Nasri, Anthony Emanuel Chifor, John James Hayward, Seyedeh Maryamdokht Taimoory, Mohadeseh Dashti-Pour
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Abstract
In a preferred embodiment, there is provided a protecting group for protecting the thiol side chain of a cysteine residue, the protecting group comprising a Diels-Alder cycloadduct of a furan and a maleimide, and optionally, a linker interposed between the thiol side chain and the Diels-Alder cycloadduct.
Claims7
A protected cysteine having structural formula 9 or 10:
- wherein
- X and Y are independently of each other oxygen, sulfur, nitrogen or phosphorus;
- R1 and R2 are independently of each other hydrogen, hydroxyl, halo, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, formyl, haloformyl, carbonyl, carboxyl, alkoxy, alkoxycarbonyl, (alkoxycarbonyl)oxy, carbamoyl, amino, amido, imino, imido, azo, cyanato, isocyanato, cyano, nitro, sulfanyl, thiocyanato or phosphono, each of which is optionally substituted;
- R3 and R4 are independently each other hydrogen or a protecting group;
- and
- n is an integer between 1 and 12, inclusive.
3 more elements
Dependencies are inferred from the claim text.