Boc-S-4-methylbenzyl-L-cysteine
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Boc-S-4-methylbenzyl-L-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002885
CAS number
61925-77-7
Molecular Formula
C16H23NO4S
Molecular Weight
325.40
Boc-S-4-methylbenzyl-L-cysteine
IUPAC Name
(2R)-3-[(4-methylphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Cys(pMeBzl)-OH
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.181±0.06 g/cm3(Predicted)
Melting Point
68-92 °C
Boiling Point
493.8±45.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C16H23NO4S/c1-11-5-7-12(8-6-11)9-22-10-13(14(18)19)17-15(20)21-16(2,3)4/h5-8,13H,9-10H2,1-4H3,(H,17,20)(H,18,19)/t13-/m0/s1
InChI Key
CUNVVZWSABRKAL-ZDUSSCGKSA-N
Canonical SMILES
CC1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OC(C)(C)C

Boc-S-4-methylbenzyl-L-cysteine is a synthetic derivative of the naturally occurring amino acid cysteine. It is characterized by the presence of a tert-butyloxycarbonyl (Boc) protecting group attached to the amino group, and a 4-methylbenzyl group on the sulfur atom of the cysteine. This compound plays a significant role in peptide synthesis, serving as a building block for more complex molecules. The Boc group is particularly useful in preventing unwanted side reactions during peptide bond formation, making the synthesis process more efficient and controllable.

One of the key applications of Boc-S-4-methylbenzyl-L-cysteine is in the realm of pharmaceutical development, particularly in the synthesis of peptide-based drugs. Polypeptides and proteins are essential components of many therapeutic agents, and Boc-S-4-methylbenzyl-L-cysteine acts as a crucial intermediary in their production. Its ability to protect the amino and thiol groups during synthesis allows for precise manipulation of these molecules, facilitating the creation of stable and effective pharmaceutical compounds with desired therapeutic properties.

Another prominent application of Boc-S-4-methylbenzyl-L-cysteine is in the study and development of biochemical assays. The compound is often utilized in the creation of synthetic peptides that serve as substrates or inhibitors in enzyme assays. This application is vital for exploring the activity of various enzymes, understanding their role in biological processes, and identifying potential targets for drug development. The stability and specificity that Boc-S-4-methylbenzyl-L-cysteine provides to synthetic peptides enhance the reliability and accuracy of these biochemical experiments.

Boc-S-4-methylbenzyl-L-cysteine is also instrumental in the production of specialty polymers. These polymers, often utilized in biomedical applications such as drug delivery systems and tissue engineering, require precise structural configurations. The use of Boc-S-4-methylbenzyl-L-cysteine in their synthesis ensures that the polymer chains have specific properties like biocompatibility and controlled degradability. The unique structural features of this compound contribute to the fine-tuning of polymer characteristics, enabling innovations in material science and engineering.

Lastly, Boc-S-4-methylbenzyl-L-cysteine finds application in the field of chemical biology, particularly in the design of chemically modified proteins. By incorporating this compound into protein structures, researchers can introduce functional modifications that allow for the study of protein interactions, dynamics, and functions within a biological context. This application is pivotal in advancing our understanding of complex biological systems and developing novel therapeutic strategies that target protein functions in disease processes.

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