Boc-S-methyl-L-cysteine
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Boc-S-methyl-L-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002896
CAS number
16947-80-1
Molecular Formula
C9H17NO4S
Molecular Weight
235.70
Boc-S-methyl-L-cysteine
IUPAC Name
(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-methylsulfanylpropanoic acid
Synonyms
Boc-L-Cys(Me)-OH; N-(TERT-BUTOXYCARBONYL)-S-METHYL-L-CYSTEINE; (R)-2-(tert-butoxycarbonylamino)-3-(methylthio)propanoic acid
Appearance
White solid
Purity
≥ 97%
Density
1.185±0.06 g/cm3(Predicted)
Melting Point
71-73 °C
Boiling Point
388.7±37.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C9H17NO4S/c1-9(2,3)14-8(13)10-6(5-15-4)7(11)12/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m0/s1
InChI Key
WFDQTEFRLDDJAM-LURJTMIESA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSC)C(=O)O

Boc-S-methyl-L-cysteine, an amino acid derivative commonly employed in peptide synthesis and various biochemical applications, serves diverse roles in scientific endeavors. Here are four key applications of Boc-S-methyl-L-cysteine:

Peptide Synthesis: Found as a crucial building block in peptide and protein synthesis, Boc-S-methyl-L-cysteine plays a pivotal role. Its safeguarded thiol group ensures the accurate formation of peptide bonds, staving off unwanted side reactions. Researchers utilize this compound extensively to introduce cysteine residues into peptides, enhancing the creation of disulfide bridges and stabilizing protein structures with finesse.

Chemical Biology Studies: Boc-S-methyl-L-cysteine finds its place in chemical biology as a vital tool for investigating protein functions and interactions. By integrating this derivative into peptides, scientists create probes or alter proteins to delve into their roles within biological processes. These investigations yield valuable insights into enzyme mechanisms, protein folding intricacies, and signaling pathway complexities.

Drug Development: In the realm of drug development, Boc-S-methyl-L-cysteine emerges as a key player in crafting peptide-based therapeutics with enhanced stability and bioavailability. Its distinctive chemical structure allows for the development of peptide analogs tailored for tackling diseases like cancer, diabetes, and infectious diseases.

Proteomics Research: In the domain of proteomics, Boc-S-methyl-L-cysteine proves its mettle by serving as a versatile tool for labeling and modifying proteins. The selective deprotection of its thiol group under mild conditions enables site-specific conjugation with other molecules or tags. This application is vital for conducting mass spectrometry-based studies, unraveling protein modifications, and discerning the intricate web of protein interactions that govern cellular processes.

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