N,N'-Di(t-butoxycarbonyl)cystamine
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N,N'-Di(t-butoxycarbonyl)cystamine

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A building block for the synthesis of thioethyl-modified peptides.

Category
BOC-Amino Acids
Catalog number
BAT-003055
CAS number
67385-10-8
Molecular Formula
C14H28N2O4S2
Molecular Weight
352.51
N,N'-Di(t-butoxycarbonyl)cystamine
IUPAC Name
tert-butyl N-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate
Synonyms
Di-Boc-Cystamine; (Boc-NH-EtS)2; Bis-Boc-cystamine; N,N'-Bis-tert-butoxycarbonyl-cystamine; tert-butyl N-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate; [2-(2-tert-butoxycarbonylamino-ethylsulfanyl)-thioethyl]carbamic acid tert-butyl ester; di-tert-Butyl(disulfanediylbis(ethane-2,1-diyl))dicarbamate; tert-butyl 2,2'-disulfanediylbis(ethane-2,1-diyl)dicarbamate; N,N-di-(tert-butyloxycarbonyl)-cystamine
Appearance
White powder
Purity
≥ 98% (TLC)
Density
1.128 g/cm3
Melting Point
118-122 °C
Boiling Point
477.2 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H28N2O4S2/c1-13(2,3)19-11(17)15-7-9-21-22-10-8-16-12(18)20-14(4,5)6/h7-10H2,1-6H3,(H,15,17)(H,16,18)
InChI Key
HBTMWZADMHBLMY-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCCSSCCNC(=O)OC(C)(C)C

N,N’-Di(t-butoxycarbonyl)cystamine, also known as Boc-cystamine, is a valuable reagent in synthetic and medicinal chemistry. Here are some key applications of N,N’-Di(t-butoxycarbonyl)cystamine:

Peptide Synthesis: Boc-cystamine is commonly used in peptide synthesis as a protecting group for cysteine residues. By temporarily masking the thiol group of cysteine, it prevents unwanted side reactions during peptide chain assembly. This facilitates the efficient synthesis of cysteine-containing peptides with high purity and yield.

Drug Development: In medicinal chemistry, Boc-cystamine is used to create prodrugs with improved stability and bioavailability. By conjugating active drugs to Boc-cystamine, researchers can enhance the pharmacokinetic properties of therapeutic compounds. Once in the body, the Boc group is removed, releasing the active drug at the target site.

Bioconjugation: Boc-cystamine is employed in bioconjugation techniques to create stable linkages between biomolecules. Its disulfide linkage allows for the controlled release of conjugated molecules under reductive conditions. This is useful in the development of targeted drug delivery systems and diagnostic agents.

Chemical Biology: In chemical biology research, Boc-cystamine is used to study redox-sensitive processes and protein folding. By incorporating Boc-cystamine into proteins, researchers can investigate how disulfide bond formation influences protein structure and function. This aids in understanding disease mechanisms related to oxidative stress and misfolded proteins.

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