25129-20-8

Basic information

• Product Name: N,N'-DIBENZOYL-L-CYSTINE
• Synonyms: BENZOYL-L-CYSTINE (DI);N-BENZOYL-L-CYSTINE;N,N'-DIBENZOYL-L-CYSTINE;N,N-Dibenzoyl-L-Cystine>96%;DIBENZOYLCYSTINE;Einecs 246-640-6;L-N,N'-Dibenzoylcystine
• CAS NO: 25129-20-8
• Molecular Formula: C₂₀H₂₀N₂O₆S₂
• Molecular Weight: 448.51
• EINECS: 246-640-6
• Product Categories: Amino Acids;Amino Acid Derivatives;Cysteine/Cystine;Peptide Synthesis
• Mol File: 25129-20-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 195-200 °C (dec.)
• Boiling Point: 814.3 °C at 760 mmHg
• Flash Point: 446.3 °C
• Appearance: /
• Density: 1.423
• PKA: 3.06±0.10(Predicted)
• BRN: 2068210
• CAS DataBase Reference: N,N'-DIBENZOYL-L-CYSTINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIBENZOYL-L-CYSTINE(25129-20-8)
• EPA Substance Registry System: N,N'-DIBENZOYL-L-CYSTINE(25129-20-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 25129-20-8(Hazardous Substances Data)

Usage

Description

N,N'-Dibenzoyl-L-cystine is a synthetic compound derived from the amino acid L-cystine. It is characterized by its unique structure, where two benzoyl groups are attached to the nitrogen atoms of the L-cystine molecule. This modification enhances its chemical and biological properties, making it a versatile molecule with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
N,N'-Dibenzoyl-L-cystine is used as a reactant for the synthesis of integrin antagonists, which are important in the development of drugs targeting various diseases, including cancer and autoimmune disorders. Its unique structure allows for the formation of specific interactions with integrin receptors, modulating their activity and potentially leading to therapeutic benefits.
Used in Material Science:
N,N'-Dibenzoyl-L-cystine is used as a molecular gelator in the dissipative self-assembly of hydrogels. Its amphiphilic nature and ability to form hydrogen bonds contribute to the formation of stable supramolecular structures, which have potential applications in drug delivery, tissue engineering, and other areas.
Used in Biomedical Research:
N,N'-Dibenzoyl-L-cystine is used in the synthesis of crosslinkable hydrogels for the proliferation of encapsulated human dermal fibroblasts. These hydrogels provide a three-dimensional environment that supports cell growth and tissue regeneration, making them valuable tools in regenerative medicine and wound healing studies.
Used in Analytical Chemistry:
N,N'-Dibenzoyl-L-cystine is used in the analysis of metallo-β-lactamase inhibitors. Its ability to interact with metallo-β-lactamases, which are enzymes responsible for antibiotic resistance in bacteria, makes it a useful tool in the development of new antimicrobial agents.
Used in Biochemistry:
N,N'-Dibenzoyl-L-cystine is used in the amplification of bifunctional disulfide ligands for calmodulin, a calcium-binding protein involved in various cellular processes. Its unique structure allows for the formation of stable disulfide bonds with calmodulin, enabling the study of its interactions with other proteins and potential applications in the development of novel calmodulin-targeting drugs.

Upstream product

• 73284-29-4 (R)-2-Benzoylamino-3-((R)-2-benzoylamino-2-tert-butoxycarbonyl-ethyldisulfanyl)-propionic acid tert-butyl ester 
• 25129-20-8 N,N'-dibenzoyl-DL-cystine 
• 349-46-2 S,S-cystine 
• 98-88-4 benzoyl chloride 
• 6020-39-9 L-cystine 
• 921-01-7 D-cysteine 
• 56-89-3 L-cystine 
• 5673-91-6 dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-benzamidopropanoate) 

Downstream Products

• 7218-05-5 DL-N-benzoylcysteine 
• 25129-20-8 N,N'-bis(benzoyl)-D-cystine 
• 5673-91-6 dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-benzamidopropanoate) 
• 467444-64-0 C₂₂H₂₄N₂O₆S₂ 
• 1378941-49-1 C₂₁H₂₁NO₇S 
• 2198-64-3 N-benzoyl-L-alanine 
• 7217-84-7 2-benzamido-3-mercaptopropanoic acid 

Relevant articles and documents

Tunable induced circular dichroism in gels

The ICD phenomenon has drawn a lot of attention in recent years in applicable fields such as chiral sensing and chiroptical devices. In this work, we first gaze at the issues of thin spin-coated films not being able to deliver consistent ICD signals. A hypothesis of the underlying problem is proposed through a brief elucidation of the spin-coating process. To confirm and eliminate the uncontrollable dynamic factors with spin coating, we then dedicate our efforts to develop a new gel system based on chiral L-/D-N′,N′-Dibenzoyl-cystine. Achiral dye molecules are intercalated in a DBC gel through a “one-step” preparation procedure. Compared to the former spin-coating system, significantly improved reproducibility of the new gel system is demonstrated. Besides, the ICD signals can be customized in a broad spectral range (wavelength tunability) by substituting dye molecules. Finally, we discuss the potential applications of this interesting system.

Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions

Chemical interaction between polyphenols and thiols was investigated under radical oxidation conditions using a model cysteinyl thiol derivative, N-benzoylcysteine methyl ester. The radical oxidation was carried out with a stoichiometric amount of 2,2-diphenyl-1-picrylhydrazyl (DPPH), and the decreases in the amounts of polyphenols and the thiol were measured by HPLC analysis. Cross-coupling products between various polyphenols and the thiol were examined by LC-MS in reactions that showed decreases in both the polyphenols and the thiol. The LC-MS results indicated that three phenolic acid esters (methyl caffeate, methyl dihydrocaffeate, and methyl protocatechuate) and six flavonoids (kaempferol, myricetin, luteolin, morin, taxifolin, and catechin) gave corresponding thiol adducts, whereas three polyphenols (methyl ferulate, methyl sinapate, and quercetin) gave only dimers or simple oxidation products without thiol substituents. Thiol adducts of the structurally related compounds methyl caffeate and methyl dihydrocaffeate were isolated, and their chemical structures were determined by NMR analysis. The mechanism for the thiol addition was discussed on the basis of the structures of the products.

Dynamic combinatorial mass spectrometry leads to metallo-β-lactamase inhibitors

The use of protein ESI mass spectrometry under non-denaturing conditions to analyze a dynamic combinatorial library of thiols/disulfides with the BcII metallo-β-lactamase enabled the rapid identification of an inhibitor with a Ki of 1 μM. The study exemplifies the utility of protein-MS for screening dynamic mixtures of potential enzyme-inhibitors.