Boc-Cys(Trt)-NH2
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Boc-Cys(Trt)-NH2

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Category
BOC-Amino Acids
Catalog number
BAT-000787
Molecular Formula
C27H30N2O3S
Molecular Weight
462.6
IUPAC Name
tert-butyl N-[(2R)-1-amino-1-oxo-3-tritylsulfanylpropan-2-yl]carbamate
Synonyms
Boc-Cys(Trt)-NH2; DWXCPGXLNGATHN-QHCPKHFHSA-N
Storage
Store at 2-8 °C
InChI
InChI=1S/C27H30N2O3S/c1-26(2,3)32-25(31)29-23(24(28)30)19-33-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18,23H,19H2,1-3H3,(H2,28,30)(H,29,31)/t23-/m0/s1
InChI Key
DWXCPGXLNGATHN-QHCPKHFHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)N

Boc-Cys(Trt)-NH2, also known as N-Boc-S-trityl-L-cysteine amide, serves as a fundamental amino acid derivative extensively utilized in peptide synthesis and biochemical research. Here are four key applications of Boc-Cys(Trt)-NH2:

Peptide Synthesis: Essential for the solid-phase construction of peptides, Boc-Cys(Trt)-NH2 facilitates the precise assembly of peptides by protecting amino and thiol functionalities with Boc (tert-butoxycarbonyl) and Trt (trityl) groups. These protective measures enable selective deprotection steps during peptide synthesis, ensuring the accurate inclusion of cysteine residues without unwanted side reactions, resulting in peptides of exceptional purity.

Bioconjugation: Within the domain of bioconjugation, Boc-Cys(Trt)-NH2 plays a crucial role in forming peptide and protein conjugates. By selectively deprotecting the thiol group of cysteine, researchers can create disulfide bonds or conjugate with various molecules, such as drugs, fluorescent dyes, or other peptides. This application holds significance in advancing targeted therapeutics, diagnostics, and biosensors, fueling progress in precision medicine.

Protein Engineering: In the realm of protein engineering, Boc-Cys(Trt)-NH2 assists in introducing cysteine residues into proteins through site-directed mutagenesis and chemical modification. The safeguarded nature of this amino acid derivative ensures precise positioning and protection of cysteine during protein folding and expression. This empowers researchers to explore protein structure, function, and intermolecular interactions by facilitating disulfide bond formation or attachment of functional groups, unraveling the complexities of biological systems.

Drug Development: Within the sphere of drug development, Boc-Cys(Trt)-NH2 shines as a cornerstone in crafting peptide-based drugs, where cysteine residues are vital for drug activity and stability. By incorporating Boc-Cys(Trt)-NH2 into therapeutic peptides, researchers can engineer molecules with enhanced pharmacokinetic properties and resistance to proteolytic degradation, ultimately enhancing the efficacy and durability of peptide drugs. This makes them more suitable for clinical applications.

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