N-α-(t-Butoxycarbonyl)-S-acetamidomethyl-L-cysteine DL-sulfoxide
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N-α-(t-Butoxycarbonyl)-S-acetamidomethyl-L-cysteine DL-sulfoxide

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Category
BOC-Amino Acids
Catalog number
BAT-003170
CAS number
75893-04-8
Molecular Formula
C11H20N2O6S
Molecular Weight
308.35
N-α-(t-Butoxycarbonyl)-S-acetamidomethyl-L-cysteine DL-sulfoxide
IUPAC Name
(2R)-3-(acetamidomethylsulfinyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-Cys(Acm,O)-OH
InChI
InChI=1S/C11H20N2O6S/c1-7(14)12-6-20(18)5-8(9(15)16)13-10(17)19-11(2,3)4/h8H,5-6H2,1-4H3,(H,12,14)(H,13,17)(H,15,16)/t8-,20?/m0/s1
InChI Key
RNEUQBJGDKCBAI-RQJNJCINSA-N
Canonical SMILES
CC(=O)NCS(=O)CC(C(=O)O)NC(=O)OC(C)(C)C

N-α-(t-Butoxycarbonyl)-S-acetamidomethyl-L-cysteine DL-sulfoxide, a synthetic amino acid derivative, finds diverse applications in pharmaceutical research and biochemistry. Here are four key applications:

Peptide Synthesis: A cornerstone in peptide synthesis, this compound serves as a pivotal building block, with protective groups that shield against unwanted side reactions during peptide assembly. Researchers embed it into peptide chains to unravel protein structure and function, fostering the innovation of cutting-edge therapeutics.

Protease Inhibition Studies: Delving into protease enzyme activity, N-α-(t-Butoxycarbonyl)-S-acetamidomethyl-L-cysteine DL-sulfoxide is instrumental in illuminating how proteases engage with cysteine residues. Incorporating it into substrates or inhibitors allows researchers to probe protease specificity, paving the way for the design of potent protease inhibitors as potential pharmaceutical agents.

Chemical Biology: A key player in chemical biology, this compound acts as a functionalized amino acid for probe synthesis, featuring a versatile sulfoxide group that undergoes a myriad of chemical transformations. This adaptability renders it an indispensable tool for labeling and probing studies, facilitating in-depth exploration of cellular processes and protein interactions.

Oxidative Stress Research: In the realm of oxidative stress and redox biology investigations, this compound’s sulfoxide moiety proves invaluable for detecting oxidative modifications and deciphering redox regulation within biological systems. Scientists leverage its properties to delve into the mechanisms of oxidative damage and assess the effectiveness of antioxidant interventions, shedding light on crucial aspects of cellular oxidative stress responses.

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