Boc-S-tert-butylthio-L-cysteine
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Boc-S-tert-butylthio-L-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002899
CAS number
30044-61-2
Molecular Formula
C12H23NO4S2
Molecular Weight
309.45
Boc-S-tert-butylthio-L-cysteine
IUPAC Name
(2R)-3-(tert-butyldisulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Cys(StBu)-OH; Boc-S-tert-butylmercapto-L-cysteine; (R)-2-((tert-Butoxycarbonyl)amino)-3-(tert-butyldisulfanyl)propanoic acid
Appearance
White to off-white powder
Purity
≥ 98% (TLC)
Density
1.181±0.06 g/cm3(Predicted)
Melting Point
116-122 °C
Boiling Point
438.2±40.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C12H23NO4S2/c1-11(2,3)17-10(16)13-8(9(14)15)7-18-19-12(4,5)6/h8H,7H2,1-6H3,(H,13,16)(H,14,15)/t8-/m0/s1
InChI Key
PPQRALRLGBAWHD-QMMMGPOBSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSSC(C)(C)C)C(=O)O

Boc-S-tert-butylthio-L-cysteine is a chemical compound commonly used in peptide synthesis and biochemical research. Here are some key applications of Boc-S-tert-butylthio-L-cysteine:

Peptide Synthesis: Boc-S-tert-butylthio-L-cysteine is employed as a protected cysteine derivative in solid-phase peptide synthesis. The Boc (tert-butoxycarbonyl) group helps in the selective protection of the amino group while the tert-butylthio group protects the thiol group. This dual protection facilitates the stepwise synthesis of peptides by preventing unwanted reactions during chain elongation.

Protein Engineering: In protein engineering, Boc-S-tert-butylthio-L-cysteine is used to introduce cysteine residues into proteins in a controlled manner. By selectively deprotecting the thiol group, researchers can form disulfide bonds or attach other functional groups to specific cysteine sites. This is vital for creating proteins with desired structural and functional properties.

Drug Design: Boc-S-tert-butylthio-L-cysteine serves as a building block in the design of cysteine-containing drug molecules. It enables the incorporation of cysteine residues into pharmacologically active peptides and proteins, which can be crucial for binding to target receptors or enzymes. This enhances the specificity and potency of therapeutic agents.

Chemical Biology: Researchers use Boc-S-tert-butylthio-L-cysteine in chemical biology to study cysteine’s role in enzymatic mechanisms and redox biology. By incorporating this protected cysteine into model systems, scientists can investigate its reactivity and interactions in a controlled environment. This aids in understanding cysteine’s biological significance and potential as a drug target.

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