56976-06-8

Basic information

• Product Name: BOC-CYS(TBU)-OH
• Synonyms: N-Boc-S-tert-butyl-L-cysteine;Boc-(R)-2-amino-3-(S-tert-butylthio)butanoic acid;Boc-S-tert-butyl-L-cysteine≥ 99% (HPLC);T-BUTYLOXYCARBONYL-S-T-BUTYL-L-CYSTEINE;N-ALPHA-T-BUTYLOXYCARBONYL-S-T-BUTYL-L-CYSTEINE;N-ALPHA-T-BUTOXYCARBONYL-S-T-BUTYL-L-CYSTEINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-S-TERT-BUTYL-L-CYSTEINE;BOC-(S)-T-BUTYL-L-CYS
• CAS NO: 56976-06-8
• Molecular Formula: C₁₂H₂₃NO₄S
• Molecular Weight: 277.38
• Product Categories: Amino Acids
• Mol File: 56976-06-8.mol

Chemical Properties

• Appearance: /Solid
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: BOC-CYS(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-CYS(TBU)-OH(56976-06-8)
• EPA Substance Registry System: BOC-CYS(TBU)-OH(56976-06-8)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 56976-06-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BOC-CYS(TBU)-OH is used as a key building block in chemical synthesis for the development of various pharmaceuticals and bioactive compounds. Its unique structure allows for the creation of complex molecules with specific properties and functions.
Used in Peptide Chemistry:
In peptide chemistry, BOC-CYS(TBU)-OH serves as a valuable component in the synthesis of peptides and proteins. It is particularly useful in the formation of disulfide bonds, which are essential for the stability and function of many biologically active peptides and proteins.
Used in Pharmaceutical Industry:
BOC-CYS(TBU)-OH is used as an intermediate in the production of various pharmaceuticals. Its role in chemical synthesis and peptide chemistry makes it a valuable asset in the development of new drugs and therapeutic agents.
Used in Research and Development:
BOC-CYS(TBU)-OH is also utilized in research and development for the study of protein structure, function, and interactions. Its unique properties make it an essential tool in the exploration of novel biological pathways and the design of targeted therapeutic strategies.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2481-10-9 (R)-S-tert-butylcysteine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2481-09-6 S-tert-Butyl-N-acetyl-L-cysteine hydrochloride 

Downstream Products

• 115369-96-5 (R)-2-((S)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-3-tert-butylsulfanyl-propionic acid methyl ester 
• 115369-95-4 (R)-2-((R)-2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-3-tert-butylsulfanyl-propionic acid methyl ester 
• 52-90-4 L-Cysteine 

Relevant articles and documents

Cysteine-based fluorescence "turn-on" sensors for Cu2+and Ag+

We designed and synthesized twometal ion binding molecules 3a and 3b based on cysteine. In 3a, pyrene is used as a fluorescent probe, while 3b contains tryptophan, which acts as a fluorescent probe as well as facilitates metal ion binding. Detailed spectroscopic, calorimetric, microscopic and computational studies revealed the binding mode and the plausible structures of the complexes.

tert-Butyl group as thiol protection in peptide synthesis

S-tert-Butylcysteine was obtained by a new method. A number of its N-protected derivatives and esters were synthesized. Syntheses of several peptides containing tert-butyl and acetamidomethyl or benzyl thioethers of cysteine were carried out. The tert-butyl group was removed from the thiol group of peptides by treatment with (2-nitrophenyl)sulfenyl chloride (NpsCl). The S-(2-nitrophenyl)sulfenyl derivatives so obtained were converted either into cysteine by reduction or into cystine derivatives by disproportionation. Owing to the mild deprotection conditions and the great stability of the S-tert-butyl group, the other protecting groups, particularly those of the thiols, could be easily removed from a variety of combinations.