10389-65-8

Basic information

• Product Name: (BOC-CYS-OH)2
• Synonyms: N,N’-di-Boc-L-cystine;N,N''-Bis-(tert-butoxycarbonyl)-L-cystine;(Boc-L-Cys-OH)2;N-alpha-t-Butyloxycarbonyl-L-cystine;BOC-L-CYSTINE extrapure;Nalpha,Nalpha'-di(tert-butoxycarbonyl)-L-cystine;3,3'-Dithiobis[N-(tert-butoxycarbonyl)-L-alanine];N,N'-Bis(tert-butoxycarbonyl)cystine
• CAS NO: 10389-65-8
• Molecular Formula: C₁₆H₂₈N₂O₈S₂
• Molecular Weight: 440.53
• EINECS: 233-852-9
• Product Categories: Amino Acids
• Mol File: 10389-65-8.mol
• Article Data: 44

Chemical Properties

• Melting Point: 140-145 °C
• Boiling Point: 627.4 °C at 760mmHg
• Flash Point: 333.2 °C
• Appearance: /
• Density: 1.313 g/cm³
• Storage Temp.: Store at 0-5°C
• Solubility: Acetic Acid (Sparingly) DMSO (Slightly, Sonicated), Methanol (Slightly)
• PKA: 3.17±0.10(Predicted)
• BRN: 2229312
• CAS DataBase Reference: (BOC-CYS-OH)2(CAS DataBase Reference)
• NIST Chemistry Reference: (BOC-CYS-OH)2(10389-65-8)
• EPA Substance Registry System: (BOC-CYS-OH)2(10389-65-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 10389-65-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N,N''-Di-BOC-L-cystine, can be used for the synthesis of Toll-Like Receptor-2 agonists lipopeptides, which are potential vaccine adjuvants.

Purification Methods

Crystallise the cystine derivative from EtOAc by adding hexane [Ferraro pKEst Biochemical Preparations 13 39 1971].

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 56-89-3 L-cystine 
• 89985-91-1 tert-butyl pyridin-2-yl carbonate 
• 105678-24-8 O-(tert-butyl) S-(pyridin-2-yl)carbonothioate 
• 5068-28-0 (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 52-90-4 L-Cysteine 
• 13059-63-7 L-cystine dihydrochloride 
• 1425107-54-5 (S)-(3,5-dinitrophenyl)(2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)methanone 
• 20887-95-0 N-(tert-Butyloxycarbonyl)-L-cysteine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 172749-96-1 N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 
• 691-64-5 di-tert-butyl oxalate 
• 62982-13-2 N-t-butoxycarbonyl-S-(diphenyl-4-pyridylmethyl)-L-cysteine 

Downstream Products

• 141043-94-9 bis 
• 92278-77-8 N,N'-bis<(tert-butyloxy)carbonyl>cystine dibenzyl ester 
• 20866-21-1 dicyclohexylamine salt of N-t-butyloxycarbonyl-L-cysteine 
• 172694-22-3 N,N'-Bis(tert-butoxycarbonyl)-L-cystine bis(pentafluorophenyl) ester 
• 160978-35-8 [1-benzylcarbamoyl-2-(2-benzylcarbamoyl-2-tert-butoxycarbonylamino-ethyldisulfanyl)-ethyl]-carbamic acid tert-butyl ester 
• 77826-55-2 N,N'-bis(tert-butoxy)carbonyl-L-cystine dimethyl ester 
• 21999-36-0 BOC-Cys(Bzm)-OH 
• 1275614-59-9 C₂₂H₃₂N₂O₆S 
• 18942-46-6 N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine 
• 84888-35-7 N^α-tert-butyloxycarbonyl-(S)-9-fluorenylmethylcysteine 
• 19746-37-3 N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine 
• 61925-77-7 Boc-cysteine(4-Me-Bn) 
• 5068-28-0 (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid 
• 30044-61-2 (R)-2-((tert-butoxycarbonyl)amino)-3-(tert-butyldisulfanyl)propanoic acid 

Relevant articles and documents

Novel amphiphilic PEG-hydroxycamptothecin conjugates as glutathione-responsive prodrug nanocapsules for cancer chemotherapy

A series of novel hydroxycamptothecin (HCPT) conjugates (13a–14d), which contained a polyethylene glycol moiety and disulfide bond, were designed and synthesized in five to six steps, with overall yields of 20–39%. The anticancer activities and toxicities of these new conjugates were evaluated using an in vitro MTT assay in K562, HepG2, and HT-29 cell lines and HUVECs. The conjugates displayed enhanced antitumor activity and reduced toxicity in comparison with their parent molecule, HCPT. Among these conjugates, compound 13a exhibited 100-fold better selectivity to the tumor cells than to HUVECs. TEM and DLS experiments demonstrated that 13a formed nanosized micelles with a diameter of approximately 200?nm in aqueous solution and that the conjugate could undergo glutathione-responsive degradation to release HCPT at the tumor site. The improved potency and reduced toxicity of these conjugates may be caused by the enhanced permeation and retention (EPR) effect of nanoparticles.

Zinc-acetic acid reductive cyclisation in a two-step synthesis of the S1-N10 nine-membered lactone core of ent-griseoviridin

The synthesis of the S1-N10 nine-membered lactone core 28 of enf-griseoviridin is reported. Starting from cystine derivative 25, encompassing a terminal ynoate, treatment under Zn/AcOH conditions led to the formation of lactone 28 in 12% yield. Therefore, the lactone moiety of enf-griseoviridin is obtained in 10.7% overall yield for two steps. An access to the corresponding 5-epi-griseoviridin lactone 29 is also described.

Structure-activity relationships in toll-like receptor 2-agonists leading to simplified monoacyl lipopeptides

Toll-like receptor 2-agonistic lipopeptides typified by S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-R-cysteinyl-S-serine (PAM2CS) compounds are potential vaccine adjuvants. In continuation of previously reported structure-activity relationships on this chemotype, we have determined that at least one acyl group of optimal length (C16) and an appropriately oriented ester carbonyl group is essential for TLR2-agonistic activity. The spacing between one of the palmitoyl ester carbonyl and the thioether is crucial to allow for an important H-bond, which observed in the crystal structure of the lipopeptide:TLR2 complex; consequently, activity is lost in homologated compounds. Penicillamine-derived analogues are also inactive, likely due to unfavorable steric interactions with the carbonyl of Ser 12 in TLR2. The thioether in this chemotype can be replaced with a selenoether. Importantly, the thioglycerol motif can be dispensed with altogether and can be replaced with a thioethanol bridge. These results have led to a structurally simpler, synthetically more accessible, and water-soluble analogue possessing strong TLR2-agonistic activities in human blood.

Cationic gemini lipids with cyclen headgroups: Interaction with DNA and gene delivery abilities

A series of novel 1,4,7,10-tetraazacyclododecane (cyclen)-based gemini cationic lipids were synthesized, and l-cystine was used as backbone between the two amphiphilic units. The liposomes formed from the lipids and DOPE could efficiently condense plasmid DNA into nanoparticles with suitable size and zeta-potentials, which might be suitable for gene transfection. These lipids were applied as non-viral gene delivery vectors, and their structure-activity relationship was studied. It was found that both the hydrophobic tails and the linking group could largely influence the transfection efficiency, and the oleylamine derived lipid gave the best transfection results, which were close to the commercially available transfection reagent lipofectamine 2000. The gemini structure would favor the gene transfection, and the transfection efficiency of the gemini lipid was much higher than the mono counterpart. Besides, these lipids have very low cytotoxicity, suggesting their good biocompatibility. Results indicate that such gemini lipids might be promising non-viral gene delivery vectors. This journal is

t-BUTYL 2-PYRIDYL CARBONATE. A USEFUL REAGENT FOR t-BUTOXYLATION OF AMINO ACIDS

t-Butyl 2-pyridyl carbonate, a stable crystalline compound, is found to be very efficient in the t-butoxycarbonylation of amino acids.

Reactions of 1,3-Diketones with a Dipeptide Isothiazolidin-3-one: Toward Agents That Covalently Capture Oxidized Protein Tyrosine Phosphatase 1B

Protein tyrosine phosphatase 1B (PTP1B) is a validated therapeutic target for the treatment of type 2 diabetes; however, the enzyme has been classified by some as an "undruggable target". Here we describe studies directed toward the development of agents that covalently capture the sulfenyl amide "oxoform" of PTP1B generated during insulin signaling events. The sulfenyl amide residue found in oxidized PTP1B presents a unique electrophilic sulfur center that may be exploited in drug and probe design. Covalent capture of oxidized PTP1B could permanently disable the intracellular pool of enzyme involved in regulation of insulin signaling. Here, we employed a dipeptide model of oxidized PTP1B to investigate the nucleophilic capture of the sulfenyl amide residue by structurally diverse 1,3-diketones. All of the 1,3-diketones examined here reacted readily with the electrophilic sulfur center in the sulfenyl amide residue to generate stable covalent attachments. Several different types of products were observed, depending upon the substituents present on the 1,3-diketone. The results provide a chemical foundation for the development of agents that covalently capture the oxidized form of PTP1B generated in cells during insulin signaling events.

Cystine cholesterol gel factor and preparation method thereof

The cystine cholesterol gel factor is obtained by taking natural product cholesterol and cystine as a raw material and carrying out chemical reaction. The invention also discloses a supramolecular gel which is prepared from the gel factors in benzene solvents. The micro-morphology is a regular nanobelt or nano fiber network structure in a solvent such as n-propanol or cyclohexane. Raw materials used in the preparation process of the gel factor and the supramolecular gel belong to natural small molecule compounds, and have the advantages of wide sources, good biocompatibility, unique structure and the like, and exhibit better ion selective recognition and reduction response characteristics. The gel system has good biocompatibility and environmental friendliness, provides a new idea for construction of the intelligent response gel material, and provides a new reference for expanding the application of the cystine and the cholesterol natural small molecule compound in the supermolecule field.

COMPOUNDS AND COMPOSITIONS COMPRISING THE SAME FOR TREATING HYPERTENSION OR HEART FAILURE

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