CAS 10389-65-8

N,N′-Bis(tert-butoxycarbonyl)-L-cystine

Description:

N,N′-Bis(tert-butoxycarbonyl)-L-cystine is a synthetic derivative of the amino acid cystine, characterized by the presence of two tert-butoxycarbonyl (Boc) protecting groups attached to the amino groups of cystine. This compound is typically used in peptide synthesis and as a protecting agent in organic chemistry, particularly for the functional groups of amino acids. The tert-butoxycarbonyl groups enhance the stability of the amino groups during chemical reactions, allowing for selective modifications. N,N′-Bis(tert-butoxycarbonyl)-L-cystine is a white to off-white solid, soluble in organic solvents such as dichloromethane and dimethylformamide, but less soluble in water. Its molecular structure includes sulfur atoms from the cystine backbone, which can participate in redox reactions, making it relevant in biochemical applications. The compound is sensitive to moisture and should be stored in a cool, dry place to maintain its integrity. Overall, it serves as a valuable intermediate in the synthesis of more complex peptides and proteins.

Formula: C₁₆H₂₈N₂O₈S₂

InChI: InChI=1S/C16H28N2O8S2/c1-15(2,3)25-13(23)17-9(11(19)20)7-27-28-8-10(12(21)22)18-14(24)26-16(4,5)6/h9-10H,7-8H2,1-6H3,(H,17,23)(H,18,24)(H,19,20)(H,21,22)/t9-,10-/m0/s1

InChI key: InChIKey=MHDQAZHYHAOTKR-UWVGGRQHSA-N

SMILES: [C@H](NC(OC(C)(C)C)=O)(CSSC[C@H](NC(OC(C)(C)C)=O)C(O)=O)C(O)=O

Synonyms:

• (Boc-Cys-OH)
• (Boc-Cys-OH)2
• (Boc-Cys-OH)2 (Disulfide bond)
• <span class="text-smallcaps">L</span>-Cystine, N,N′-bis[(1,1-dimethylethoxy)carbonyl]-
• Cystine, N,N′-dicarboxy-, N,N′-di-tert-butyl ester
• Cystine, N,N′-dicarboxy-, N,N′-di-tert-butyl ester, <span class="text-smallcaps">L</span>-
• N,N'-Bis-Boc-L-cystine
• N,N'-bis(tert-butoxycarbonyl)-L-cystine
• N,N'-bis(tert-butoxycarbonyl)cystine
• N,N-bis(T-boc)-L-cystine
• N,N′-Bis(tert-butoxycarbonyl)-<span class="text-smallcaps">L</span>-cysteine
• N,N′-Bis(tert-butoxycarbonyl)-<span class="text-smallcaps">L</span>-cystine
• N,N′-Bis[(1,1-dimethylethoxy)carbonyl]-<span class="text-smallcaps">L</span>-cystine
• N,N′-Di(tert-butoxycarbonyl)-<span class="text-smallcaps">L</span>-cystine
• N,N′-Di-BOC-<span class="text-smallcaps">L</span>-cystine
• NSC 164046
• Cystine, N,N′-dicarboxy-, N,N′-di-tert-butyl ester, L-
• L-Cystine, N,N′-bis[(1,1-dimethylethoxy)carbonyl]-

(Boc-Cys-OH)₂

CAS: 10389-65-8

Tai et al. could obtain asymmetric cystine peptides from (Boc-Cys-OH)₂ by enzymatic catalysis with immobilized papain. Oxidation of Boc-cystine with hydrogen peroxide in the presence of Na wolframate yielded the sodium salt of Boc-cysteic acid. Boc cystine benzyl ester was used as educt for obtaining S-isoacyl dipeptide building blocks.

Formula: C₁₆H₂₈N₂O₈S₂

Purity: > 98%

Color and Shape: White

Molecular weight: 440.54

Ref: 01-4001680

L-Cystine, N,N'-bis[(1,1-dimethylethoxy)carbonyl]-

CAS: 10389-65-8

Formula: C₁₆H₂₈N₂O₈S₂

Purity: 95%

Color and Shape: Solid

Molecular weight: 440.5321

Ref: IN-DA00HA7R

N,N’-Di-Boc-L-Cystine

CAS: 10389-65-8

N,N’-Di-Boc-L-Cystine

Purity: 98%

Molecular weight: 440.53g/mol

Ref: 54-OR1014091

(Boc-Cys-OH)2

CAS: 10389-65-8

Molecular weight: 440.53

Ref: 7W-GM1444

N,N’-Di-BOC-L-cystine

CAS: 10389-65-8

Purity: 95%

Molecular weight: 440.53

Ref: 10-F987855

BOC-L-Cystine extrapure, 99%

CAS: 10389-65-8

Formula: C₁₆H₂₈N₂O₈S₂

Purity: min. 99%

Color and Shape: White, Crystalline powder

Molecular weight: 440.60

Ref: SR-14930

(Boc-Cys-OH)2

CAS: 10389-65-8

Formula: C₁₆H₂₈N₂O₈S₂

Purity: 95%

Color and Shape: Solid

Molecular weight: 440.53

Ref: 10-F547732

N,N'-Di-BOC-L-cystine

Controlled Product

CAS: 10389-65-8

Applications N,N'-Di-BOC-L-cystine, can be used for the synthesis of Toll-Like Receptor-2 agonists lipopeptides, which are potential vaccine adjuvants.
References Agnihotri, G., et al.: J. Med. Chem., 54, 8148 (2011);

Formula: C₁₆H₂₈N₂O₈S₂

Color and Shape: Neat

Molecular weight: 440.53

Ref: TR-D421995