L-Cystine bis(tert-butyl ester) dihydrochloride
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L-Cystine bis(tert-butyl ester) dihydrochloride

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Category
L-Amino Acids
Catalog number
BAT-003970
CAS number
38261-78-8
Molecular Formula
C14H28N2O4S2·2HCl
Molecular Weight
425.44
L-Cystine bis(tert-butyl ester) dihydrochloride
IUPAC Name
tert-butyl (2R)-2-amino-3-[[(2R)-2-amino-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]disulfanyl]propanoate;dihydrochloride
Synonyms
(H-L-Cys-OtBu)2 2HCl; tert-butyl (2R)-2-amino-3-[[(2R)-2-amino-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]disulfanyl]propanoate,dihydrochloride; (2R,2'R)-Di-tert-butyl 3,3'-disulfanediylbis(2-aminopropanoate) dihydrochloride
Appearance
White solid
Purity
≥ 97% (TLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H28N2O4S2.2ClH/c1-13(2,3)19-11(17)9(15)7-21-22-8-10(16)12(18)20-14(4,5)6;;/h9-10H,7-8,15-16H2,1-6H3;2*1H/t9-,10-;;/m0../s1
InChI Key
QEFUTIQOPVMOJQ-BZDVOYDHSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CSSCC(C(=O)OC(C)(C)C)N)N.Cl.Cl

L-Cystine bis(tert-butyl ester) dihydrochloride, a chemical reagent widely utilized in bioscience and pharmaceutical research, finds diverse applications in the following four areas:

Peptide Synthesis: Serving as a safeguarded version of cystine during peptide synthesis, L-Cystine bis(tert-butyl ester) dihydrochloride plays a pivotal role by preventing the formation of unwanted disulfide bonds. This ensures the production of intricately structured peptide chains with utmost purity and efficiency.

Drug Development: Positioned at the forefront of pharmaceutical research, L-Cystine bis(tert-butyl ester) dihydrochloride proves invaluable in the creation of cystine-containing drug candidates. Its protected form simplifies handling and integration into drug molecules, essential for yielding stable, effective, and safe therapeutic agents.

Antioxidant Studies: Delving into the antioxidant properties of cystine and cysteine derivatives, L-Cystine bis(tert-butyl ester) dihydrochloride emerges as a key player in investigating oxidative stress and its impact on cellular models. This exploration aids in unraveling mechanisms of cellular defense and injury, paving the way for interventions against diseases linked to oxidative stress.

Protein Modification: Within the realm of bioscience, L-Cystine bis(tert-butyl ester) dihydrochloride finds application in the introduction of cystine into proteins, facilitating the study of protein structure and function. Its protective ester groups permit controlled insertion without premature oxidation, enabling the generation of proteins with tailored properties for both research and therapeutic purposes.

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