Boc-S-acetamidomethyl-D-cysteine
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Boc-S-acetamidomethyl-D-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002888
CAS number
138775-00-5
Molecular Formula
C11H20N2O5S
Molecular Weight
292.30
Boc-S-acetamidomethyl-D-cysteine
IUPAC Name
(2S)-3-(acetamidomethylsulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-D-Cys(Acm)-OH; (S)-3-((Acetamidomethyl)thio)-2-((tert-butoxycarbonyl)amino)propanoic acid
Appearance
White powder
Purity
≥ 98% (HPLC)
Melting Point
108-116 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C11H20N2O5S/c1-7(14)12-6-19-5-8(9(15)16)13-10(17)18-11(2,3)4/h8H,5-6H2,1-4H3,(H,12,14)(H,13,17)(H,15,16)/t8-/m1/s1
InChI Key
HLCTYBOTPCIHTG-MRVPVSSYSA-N
Canonical SMILES
CC(=O)NCSCC(C(=O)O)NC(=O)OC(C)(C)C

Boc-S-acetamidomethyl-D-cysteine, a chemical compound widely utilized in peptide synthesis and biochemistry, serves as a key player in various applications. Here are its four primary applications:

Peptide Synthesis: Acting as a protective group for cysteine residues during peptide assembly, Boc-S-acetamidomethyl-D-cysteine shields the thiol group, thereby averting undesired side reactions. This protective action ensures the precise construction of peptides, especially crucial for synthesizing intricate peptide sequences with implications for both research endeavors and therapeutic interventions.

Protein Engineering: Embracing the realm of protein modification, Boc-S-acetamidomethyl-D-cysteine facilitates the tailored alteration of proteins. By selectively removing its protective group, specific functional groups can be introduced at cysteine sites, fostering the creation of proteins endowed with novel functionalities or enhanced properties tailored for diverse biomedical applications.

Pharmaceutical Research: Empowering pharmaceutical investigations, this compound enables the development of cysteine-incorporating peptides crucial for drug discovery endeavors. These tailored peptides can serve as inhibitors, mimetics, or therapeutic agents, targeting precise proteins or pathways, thereby offering a valuable resource for the design of innovative treatments catering to ailments such as cancer and autoimmune disorders.

Structural Biology: Playing a pivotal role in structural biology inquiries, Boc-S-acetamidomethyl-D-cysteine contributes to unraveling protein structures with finesse. Through selective labeling of cysteine residues, researchers harness advanced techniques like X-ray crystallography and NMR spectroscopy to scrutinize protein conformation and interactions, unearthing critical insights into protein functionality.

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