Boc-S-4-methoxybenzyl-L-cysteine
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Boc-S-4-methoxybenzyl-L-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002883
CAS number
18942-46-6
Molecular Formula
C16H23NO5S
Molecular Weight
341.40
Boc-S-4-methoxybenzyl-L-cysteine
IUPAC Name
(2R)-3-[(4-methoxyphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Cys(pMeOBzl)-OH
Appearance
White to off-white powder
Purity
≥ 98% (HPLC, TLC)
Density
1.205±0.06 g/cm3(Predicted)
Melting Point
68-77 °C
Boiling Point
514.0±50.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C16H23NO5S/c1-16(2,3)22-15(20)17-13(14(18)19)10-23-9-11-5-7-12(21-4)8-6-11/h5-8,13H,9-10H2,1-4H3,(H,17,20)(H,18,19)/t13-/m0/s1
InChI Key
VRTXRNJMNFVTOM-ZDUSSCGKSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSCC1=CC=C(C=C1)OC)C(=O)O

Boc-S-4-methoxybenzyl-L-cysteine is a protected amino acid derivative used in peptide synthesis and other biochemical applications. Here are some key applications of Boc-S-4-methoxybenzyl-L-cysteine:

Peptide Synthesis: Boc-S-4-methoxybenzyl-L-cysteine is commonly employed in the solid-phase synthesis of peptides. The Boc (tert-butyloxycarbonyl) group protects the amino group during synthesis, preventing unwanted side reactions. Once the peptide chain is assembled, the protecting groups can be removed to yield the desired peptide.

Protein Engineering: This compound is valuable in protein engineering efforts where precise modifications of protein sequences are required. By incorporating Boc-S-4-methoxybenzyl-L-cysteine into a growing peptide or protein sequence, researchers can introduce specific functional groups or structural motifs. This facilitates the study of protein function and interactions.

Drug Design: In medicinal chemistry, Boc-S-4-methoxybenzyl-L-cysteine is used to develop and optimize peptide-based drugs. Peptide drugs often require specific modifications to improve stability, bioavailability, and target specificity. Using protected amino acid derivatives like this one allows for precise control over the drug’s properties.

Enzyme Inhibition Studies: Boc-S-4-methoxybenzyl-L-cysteine can be used to synthesize enzyme inhibitors that target cysteine residues in enzyme active sites. By creating modified peptides that can interfere with enzyme function, researchers can study enzyme mechanisms and identify potential drug candidates. This approach is valuable for developing inhibitors against enzymes involved in diseases.

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