Boc-S-4-methoxybenzyl-D-cysteine
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Boc-S-4-methoxybenzyl-D-cysteine

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Category
BOC-Amino Acids
Catalog number
BAT-002882
CAS number
58290-35-0
Molecular Formula
C16H23NO5S
Molecular Weight
341.40
Boc-S-4-methoxybenzyl-D-cysteine
IUPAC Name
(2S)-3-[(4-methoxyphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-D-Cys(pMeOBzl)-OH
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.205 g/cm3
Melting Point
68-74 °C
Boiling Point
514°C at 760 mmHg
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-/m1/s1
InChI Key
VRTXRNJMNFVTOM-CYBMUJFWSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSCC1=CC=C(C=C1)OC)C(=O)O

Boc-S-4-methoxybenzyl-D-cysteine, a specialized amino acid derivative, plays a pivotal role in peptide synthesis and biomedical research. Here are four key applications:

Peptide Synthesis: Serving as a fundamental building block in peptide synthesis, Boc-S-4-methoxybenzyl-D-cysteine features a protective Boc (tert-butyloxycarbonyl) group that shields against unwanted reactions during peptide elongation. This safeguard ensures precise sequencing, making it an indispensable reagent for crafting peptides with tailored structural and functional attributes.

Drug Development: Embracing innovation in drug discovery, researchers harness Boc-S-4-methoxybenzyl-D-cysteine in formulating therapeutic peptides. The cysteine component facilitates the creation of disulfide bridges, essential for the stability and efficacy of bioactive peptides. This application is particularly significant in developing novel drugs targeting diverse entities like enzymes, receptors, and protein-protein interactions.

Enzyme Mechanism Studies: As a substrate analog, Boc-S-4-methoxybenzyl-D-cysteine serves as a valuable tool for probing enzyme mechanisms and active site interactions. By integrating this modified amino acid into peptide or protein constructs, scientists can unravel how enzymes perceive and process substrates. This exploration enhances comprehension of enzyme specificity and aids in designing enzyme inhibitors for targeted interventions.

Structural Biology: Within the realm of structural biology, Boc-S-4-methoxybenzyl-D-cysteine is instrumental in imposing conformational constraints on peptides and proteins. These constraints play a crucial role in delineating the three-dimensional structures of molecules using advanced techniques such as X-ray crystallography and NMR spectroscopy. Unraveling these intricate structures is pivotal for deciphering biomolecular functions and crafting efficacious therapeutic interventions.

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