Boc-S-4-methylbenzyl-D-cysteine
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Boc-S-4-methylbenzyl-D-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002884
CAS number
61925-78-8
Molecular Formula
C16H23NO4S
Molecular Weight
325.40
Boc-S-4-methylbenzyl-D-cysteine
IUPAC Name
(2S)-3-[(4-methylphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-D-Cys(pMeBzl)-OH
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.181±0.06 g/cm3(Predicted)
Melting Point
78-85 °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-/m1/s1
InChI Key
CUNVVZWSABRKAL-CYBMUJFWSA-N
Canonical SMILES
CC1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OC(C)(C)C

Boc-S-4-methylbenzyl-D-cysteine, a chemical compound widely utilized in biochemical and pharmaceutical research, boasts diverse applications. Here are four key applications:

Peptide Synthesis: A staple in solid-phase peptide synthesis, Boc-S-4-methylbenzyl-D-cysteine serves as a shielded amino acid, with its Boc (tert-butoxycarbonyl) safeguarding the amino group throughout sequential amino acid additions. This meticulous protection ensures smooth synthesis, thwarting undesired reactions and yielding impeccably pure peptides.

Protease Inhibition Studies: Acting as a foundational element, this compound aids in crafting custom inhibitors for cysteine proteases, pivotal enzymes in various biological processes. By analyzing inhibition properties of tailored peptides containing Boc-S-4-methylbenzyl-D-cysteine, researchers glean insights into enzyme mechanics and potential therapeutic avenues essential for drug development targeting ailments like cancer and parasitic infections.

Structural Biology: Integrated into peptide chains, Boc-S-4-methylbenzyl-D-cysteine facilitates investigations into protein folding and stability dynamics. The 4-methylbenzyl group introduces hydrophobic interactions, influencing protein structure and behavior. Scientists leverage this to decipher the factors governing protein conformation and stability, pivotal in drug design and protein manipulation.

Drug Delivery Systems: Embraced in targeted drug delivery design, Boc-S-4-methylbenzyl-D-cysteine enhances controlled-release systems. Infused into polymer backbones or nanocarriers, this compound enables tailored systems with precise delivery properties, augmenting therapeutic agent distribution and effectiveness, especially in cancer therapy and specialized treatments.

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