75179-29-2

Basic information

• Product Name: BOC-CYS(TRT)-OSU
• Synonyms: BOC-S-TRITYL-L-CYSTEINE N-HYDROXYSUCCINIMIDE ESTER;BOC-CYS(TRT)-OSU;N-tert-Butoxycarbonyl-S-cysteine N-hydroxysuccinimide ester;Boc-L-Cys(Trt)-OSu;N-alpha-t-Butyloxycarbonyl-S-trityl-L-cysteine succinimidyl ester;(Tert-Butoxy)Carbonyl Cys(Trt)-OSu
• CAS NO: 75179-29-2
• Molecular Formula: C₃₁H₃₂N₂O₆S
• Molecular Weight: 560.66
• Product Categories: Amino Acids
• Mol File: 75179-29-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: BOC-CYS(TRT)-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-CYS(TRT)-OSU(75179-29-2)
• EPA Substance Registry System: BOC-CYS(TRT)-OSU(75179-29-2)

Safety Data

• Hazardous Substances Data: 75179-29-2(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
BOC-CYS(TRT)-OSU is used as a building block for the formation of peptide bonds in peptide synthesis. Its protective groups ensure the stability of the cysteine amino acid during the synthesis process, preventing unwanted side reactions.
Used in Chemical Research:
In chemical research, BOC-CYS(TRT)-OSU is used as a precursor for the synthesis of various complex molecules. The deprotection of the compound under specific conditions allows for the exposure of the free cysteine amino acid, enabling further functionalization and conjugation reactions.
Used in Biological Research:
BOC-CYS(TRT)-OSU is employed in biological research for the study of protein structure and function. BOC-CYS(TRT)-OSU can be incorporated into peptides and proteins, and its deprotection allows for the investigation of the role of cysteine residues in protein folding, stability, and interactions with other biomolecules.
Used in Drug Development:
In the pharmaceutical industry, BOC-CYS(TRT)-OSU is used as a key intermediate in the synthesis of therapeutic peptides and proteins. BOC-CYS(TRT)-OSU's protective groups ensure the correct formation of peptide bonds and the preservation of the desired biological activity during the drug development process.
Used in Bioconjugation:
BOC-CYS(TRT)-OSU is utilized in bioconjugation techniques for the attachment of various functional groups, such as fluorescent tags, affinity tags, or other biomolecules, to peptides and proteins. The deprotection of the compound allows for the selective modification of the cysteine residue, enabling the development of novel bioconjugates for various applications, including diagnostics, therapeutics, and imaging.

Upstream product

• 21947-98-8 N-tert-butyloxycarbonyl-S-trityl-L-cysteine 
• 2799-07-7 S-trityl-L-cysteine 
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Downstream Products

• 116505-40-9 N^α-tert-Butyloxycarbonyl,S-trityl-cysteyl-prolyl-arginine 
• 587854-43-1 Fmoc-Lys[N-Boc-Cys(Trt)]-OH 
• 406728-64-1 {1-[2-(3,4-dihydroxyphenyl)ethyl]carbamoyl-2-(tritylsulfanyl)ethyl}carbamic acid tert-butyl ester 
• 1370349-51-1 2-amino-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(tritylsulfanyl)propionamide 
• 406727-56-8 3-(3,4-dihydroxyphenyl)-N-{1-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]-2-(tritylsulfanyl)ethyl}acrylamide 
• 1370349-53-3 2-[2-(3,4-dihydroxyphenyl)acetylamino]-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(tritylsulfanyl)propionamide 
• 149207-19-2 methyl N-(N-Boc-S-trityl-(R)-cysteinyl)-(R)-penicillamine 
• 149207-20-5 methyl N-(N-Boc-S-trityl-(R)-cysteinyl)-(S)-penicillamine 

Relevant articles and documents

Early-Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2-Cyanobenzothiazole/1,2-Aminothiol Bioorthogonal Click Reaction

Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2-cyanobenzothiazole (CBT) and a 1,2-aminothiol moiety. This methodology allows for the facile and site-specific modificat

Two bifunctional desferrioxamine chelators for bioorthogonal labeling of biovectors with zirconium-89

We report two bifunctional chelators, DFO-Cys and DFO-CBT, to label biovectors with zirconium-89 according to the 2-cyanobenzothiazole/1,2-aminothiol cycloaddition. Their features are high labeling yields, rapid and efficient bioconjugation, metabolically stable luciferin-based end products, and applicability to orthogonal two-step labeling of sensitive biomolecules.

Multifunctional imaging cross-linked stable nanometer drug-loading micelles and preparation method thereof

The present invention discloses multifunctional imaging cross-linked stable nanometer drug-loading micelles and a preparation method thereof. The preparation method comprises: adding 200 mg of an amphiphilic drug carrier mPEG-S-Trityl-Cys-Dopa and a hydrophobic anti-cancer drug to an organic solvent, dissolving, and carrying out dialysis by using a dialysis bag to remove free Fe; carrying out centrifugation, and filtering the supernatant by using a 0.45 [mu]m microporous filtration membrane; and carrying out freeze drying on the filtrate, wherein the freeze-dried product is the multifunctional imaging cross-linked stable nanometer drug-loading micelles mPEG-S-Trityl-Cys-Dopa-Fe/hydrophobic anti-cancer drug. According to the present invention, the obtained nanometer micelles have the stability and the pH-sensitivity, and can be visible by MRI, can break through the single-function mode of the traditional drug delivery system, can integrate the MRI imaging function and the drug carrier function, and can achieve the synchronous diagnosis and treatment of cancers.

Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities

Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test. As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group.

Cell permeable ITAM constructs for the modulation of mediator release in mast cells

Spleen tyrosine kinase (Syk) is essential for high affinity IgE receptor (FcεRI) mediated mast cell degranulation. Once FcεRI is stimulated, intracellular ITAM motifs of the receptor are diphosphorylated (dpITAM) and Syk is recruited to the receptor by binding of the Syk tandem SH2 domain to dpITAM, resulting in activation of Syk and, eventually, degranulation. To investigate intracellular effects of ITAM mimics, constructs were synthesized with ITAM mimics conjugated to different cell penetrating peptides, i.e. Tat, TP10, octa-Arg and K(Myr)KKK, or a lipophilic C12-chain. In most constructs the cargo and carrier were linked to each other through a disulfide bridge, which is convenient for combining different cargos with different carriers and has the advantage that the cargo and the carrier may be separated by reduction of the disulfide once it is intracellular. The ability of these ITAM constructs to label RBL-2H3 cells was assessed using flow cytometry. Fluorescence microscopy showed that the octa-Arg-SS-Flu-ITAM construct was present in various parts of the cells, although it was not homogeneously distributed. In addition, cell penetrating constructs without fluorescent labels were synthesized to examine degranulation in RBL-2H3 cells. Octa-Arg-SS-ITAM stimulated the mediator release up to 140%, indicating that ITAM mimics may have the ability to activate non-receptor bound Syk.