Boc-S-tert-butyl-L-cysteine
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Boc-S-tert-butyl-L-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002897
CAS number
56976-06-8
Molecular Formula
C12H23NO4S
Molecular Weight
277.40
Boc-S-tert-butyl-L-cysteine
IUPAC Name
(2R)-3-tert-butylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Cys(tBu)-OH; Boc-(R)-2-amino-3-(S-tert-butylthio)butanoic acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Melting Point
86-92 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C12H23NO4S/c1-11(2,3)17-10(16)13-8(9(14)15)7-18-12(4,5)6/h8H,7H2,1-6H3,(H,13,16)(H,14,15)/t8-/m0/s1
InChI Key
OGARKMDCQCLMCS-QMMMGPOBSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSC(C)(C)C)C(=O)O

Boc-S-tert-butyl-L-cysteine, a versatile chemical compound bridging organic chemistry and biochemistry, assumes a critical role in both peptide synthesis and drug development. Here are four key applications:

Peptide Synthesis: Positioned at the forefront of peptide synthesis, Boc-S-tert-butyl-L-cysteine emerges as a pivotal player with a protected thiol group that orchestrates selective deprotection, laying the groundwork for establishing essential disulfide bonds crucial for the structural integrity of peptides. This intricate process ensures the meticulous creation of peptides characterized by exceptional fidelity and functional precision, guaranteeing the precise assembly of complex peptide architectures.

Drug Development: In the realm of medicinal chemistry, Boc-S-tert-butyl-L-cysteine takes center stage as a critical precursor in synthesizing various therapeutic agents. Playing a fundamental role in crafting cysteine-containing bioactive compounds like enzyme inhibitors and receptor modulators, this compound propels the iterative cycle of drug design, optimization, and comprehensive testing. Its indispensable contribution to drug development underscores its significance in propelling therapeutic interventions with unparalleled precision.

Bioconjugation: Embraced in bioconjugation methodologies, Boc-S-tert-butyl-L-cysteine spearheads the generation of well-defined protein conjugates. Its reactive thiol group engages with maleimides or other electrophiles, facilitating the attachment of a diverse array of probes, drugs, or polymer chains to proteins. This versatile application shapes targeted therapies, diagnostic tools, and state-of-the-art biomaterials, showcasing the compound’s adaptability in enabling precise molecular interactions tailored for sophisticated biomedical applications.

Proteomics Research: Within the dynamic realm of proteomics, Boc-S-tert-butyl-L-cysteine serves as an invaluable tool for probing cysteine residues within proteins. Through selective modification and labeling, researchers delve into cysteine’s influence on protein structure and function, unveiling intricate details of protein interactions, enzymatic activities, and redox regulation mechanisms in biological systems. This nuanced investigative approach sheds light on the nuances of protein functionality, offering profound insights into critical biological processes with heightened precision.

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