Boc-Cys(StBu)-OH, CAS No. 30044-61-2

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30044-61-2

Catalog No. EBD42316

CAS 30044-61-2

Name Boc-Cys(StBu)-OH

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Basic Information

Synonyms: Boc-Cys(StBu)-OH boc-S-tert-butylmercapto-L-cysteine N-[(1,1-dimethylethoxy)carbonyl]-3-[(1,1-dimethylethyl)dithio]-L-alanine 3-tert-butyldisulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoicacid N-((1,1-Dimethylethoxy)carbonyl)-3-((1,1-dimethylethyl)dithio)-L-alanine N-(tert-butoxycarbonyl)-3-(tert-butyldisulfanyl)alanine

Molecular Formula: C12H23NO4S2

Molecular Weight: 309.45

MDL Number: MFCD00084687

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

Product Description:

Boc-S-tert-Butylthio-L-cysteine is a protected derivative of the amino acid L-cysteine. Its structure features a Boc (tert-butoxycarbonyl) group protecting the amine functionality and an S-tert-butylthio group protecting the thiol side chain. This dual protection makes it a crucial building block in peptide synthesis, particularly for the controlled introduction of cysteine residues. The primary application of this compound is in solid-phase and solution-phase peptide synthesis. The S-tert-butylthio (StBu) protecting group is stable under standard acidic Boc-deprotection conditions but can be selectively removed under reductive conditions (e.g., using phosphines like TCEP or tris(2-carboxyethyl)phosphine) to generate the free thiol. This allows for the subsequent formation of disulfide bonds, which are critical for the structure and function of many therapeutic peptides and proteins. It is widely used in research and development for producing peptides with native disulfide bridges, cyclic peptides, and peptide-drug conjugates. Its role is foundational in the synthesis of complex biomolecules where precise cysteine incorporation and disulfide pairing are required for biological activity.

Physical Properties

Melting Point: 117-119 °C

Boiling Point: 438.2 °C at 760 mmHg

Flash Point: 218.8 °C

Density: 1.181 g/cm3