Boc-β,β-dimethyl-Cys(NPys)-OH
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Boc-β,β-dimethyl-Cys(NPys)-OH

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Category
BOC-Amino Acids
Catalog number
BAT-015926
CAS number
250375-03-2
Molecular Formula
C15H21N3O6S2
Molecular Weight
403.48
Boc-β,β-dimethyl-Cys(NPys)-OH
IUPAC Name
3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(3-nitropyridin-2-yl)disulfanyl]butanoic acid
Synonyms
Boc-Pen(NPys)-OH; Boc-D-Pen(NPys)-OH; L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-[(3-nitro-2-pyridinyl)dithio]-
Purity
99%
Sequence
Boc-DL-Pen(Npys)-OH
Storage
Store at -20°C
InChI
InChI=1S/C15H21N3O6S2/c1-14(2,3)24-13(21)17-10(12(19)20)15(4,5)26-25-11-9(18(22)23)7-6-8-16-11/h6-8,10H,1-5H3,(H,17,21)(H,19,20)
InChI Key
KBMFCGVAENSRSY-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(C(=O)O)C(C)(C)SSC1=C(C=CC=N1)[N+](=O)[O-]

Boc-ββ-dimethyl-Cys(NPys)-OH, a specialized amino acid derivative utilized in peptide synthesis and biochemical research, boasts a wide array of applications.

Peptide Synthesis: Serving as a pivotal building block in the solid-phase synthesis of peptides and proteins, Boc-ββ-dimethyl-Cys(NPys)-OH plays a critical role. The Npys (nitrophenylsulfenyl) protecting group allows for selective disulfide bond formation in peptides, granting meticulous control over peptide structure and function. This level of precision is essential for probing protein-protein interactions and crafting therapeutic peptides with tailored properties.

Drug Discovery: In the realm of drug discovery, Boc-ββ-dimethyl-Cys(NPys)-OH emerges as a key player in generating peptide-based drug candidates characterized by enhanced stability and bioactivity. By modifying cysteine residues with this derivative, the pharmacokinetic properties of peptides can be optimized, elevating their potential as therapeutic agents targeting enzymes, receptors, and ion channels.

Bioconjugation: The versatility of Boc-ββ-dimethyl-Cys(NPys)-OH shines in bioconjugation procedures aimed at linking peptides with diverse molecules like polymers, nanoparticles, and other biomolecules. The selective reactivity of the Npys group allows for site-specific conjugation, facilitating the development of biomaterials and targeted delivery systems. This capability is pivotal for advancing diagnostic tools and precision therapeutics tailored to individual needs.

Protein Engineering: In the domain of protein engineering, Boc-ββ-dimethyl-Cys(NPys)-OH serves as a potent tool for introducing specific modifications into proteins to unravel structure-function relationships. By integrating this derivative into proteins, researchers can forge novel disulfide bonds or cysteine modifications, offering insights into protein stability, folding, and interactions. This in-depth exploration contributes to our comprehension of protein biophysics and informs the design of proteins with bespoke functionalities.

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