32854-09-4

Basic information

• Product Name: Dimethyl L-cystinate dihydrochloride
• Synonyms: DiMethyl L-Cystine dihydrochloride;(2R,2'R)-DiMethyl 3,3'-disulfanediylbis(2-aMinopropanoate) dihydrochloride;L-Cystine,1,1'-diMethyl ester, hydrochloride (1:2);Methyl 2-amino-3-(((R)-2-amino-3-methoxy-3-oxopropyl)disulfanyl)propanoate dihydrochloride;(L-Cys-OMe)2·2HCl;(H-L-Cys-OMe)2·2HCl (Disulfide bond);L-Cystine bis(methyl ester) dihydrochloride≥ 98% (TLC);DIMETHYL CYSTINATE 2HCL
• CAS NO: 32854-09-4
• Molecular Formula: C₈H₁₆N₂O₄S₂*2ClH
• Molecular Weight: 341.28
• EINECS: 251-261-4
• Product Categories: pharmacetical;Chemical Amines;Amine;Amino Acids & Derivatives;Sulfur & Selenium Compounds;Amino Acid Derivatives;Cysteine/Cystine;Peptide Synthesis
• Mol File: 32854-09-4.mol

Chemical Properties

• Melting Point: 182-183 °C (dec.)(lit.)
• Boiling Point: 375.5 °C at 760 mmHg
• Flash Point: 180.9 °C
• Appearance: White/Powder
• Vapor Pressure: 7.75E-06mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: DMSO, Methanol, Water
• BRN: 4727524
• CAS DataBase Reference: Dimethyl L-cystinate dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl L-cystinate dihydrochloride(32854-09-4)
• EPA Substance Registry System: Dimethyl L-cystinate dihydrochloride(32854-09-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 32854-09-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl L-cystinate dihydrochloride is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
As a white solid compound with specific chemical properties, Dimethyl L-cystinate dihydrochloride is used as a research tool in chemical laboratories. It can be employed to study the properties of similar compounds, understand their reactivity, and explore new synthetic pathways.
Used in Organic Synthesis:
Dimethyl L-cystinate dihydrochloride is used as a reagent in organic synthesis for the preparation of various organic compounds. Its unique structure and functional groups make it a valuable component in the synthesis of complex molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C8H16N2O4S2/c1-13-7(11)5(9)3-15-16-4-6(10)8(12)14-2/h5-6H,3-4,9-10H2,1-2H3/p+2/t5-,6-/m0/s1

Upstream product

• 67-56-1 methanol 
• 349-46-2 S,S-cystine 
• 56-89-3 L-cystine 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 220168-39-8 benzyl N-(benzoyloxy)benzohydroxamate 
• 13059-63-7 L-cystine dihydrochloride 

Downstream Products

• 18598-60-2 N,N'-ditrityl-D-cystine dimethyl ester 
• 3693-95-6 N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester 
• 1492-83-7 N,N'-bis(trifluoroacetyl)-L-cystine dimethyl ester 
• 77826-55-2 N,N'-bis(tert-butoxy)carbonyl-L-cystine dimethyl ester 
• 93394-80-0 methyl (6S,9R,14R)-6-benzyl-14-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-9-(methoxycarbonyl)-2,2-dimethyl-4,7-dioxo-3-oxa-11,12-dithia-5,8-diazapentadecan-15-oate 
• 157598-35-1 N,N'-bis(2'-acetoxybenzoyl)-L-cystine dimethyl ester 

Relevant articles and documents

Biosynthetic selenoproteins with genetically-encoded photocaged selenocysteines

Selenocysteine is a valuable component of both natural selenoproteins and designer biocatalysts; however the availability of such proteins is hampered by technical limitations. Here we report the first general strategy for the production of selenoproteins via genetically-encoded incorporation of a synthetic photocaged selenocysteine residue in yeast cells, and provide examples of light-controlled protein dimerization and targeted covalent labeling in vitro.

Redox-Driven Chiral Inversion of Water-Soluble Pillar[5]arene with l -Cystine Derivative in the Aqueous Medium

In the aqueous solution, l-CySS-OMe induced pS-WP5 from racemic WP5. Upon the addition of dithiothreitol as a reducing reagent to the above system, pS-WP5 was then converted to pR-WP5 for the reason that l-CySS-OMe was reduced to l-Cys-OMe. Followed by the addition of H2O2 as an oxidation reagent, pR-WP5 was converted back to pS-WP5. The chiral conformational transferring process between pR-WP5 and pS-WP5 can be easily and visually observed by reading the CD signal.

CYSTINE DIAMIDE ANALOGS FOR CYSTINURIA

This document discloses novel cystine analogs, methods of making cystine analogs, compositions containing cystine analogs and methods of using such analogs for inhibiting cystine stone formation and treatment of cystinuria.

Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source

A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.

Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity

The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).

Scalable synthesis of orthogonally protected β-methyllanthionines by indium(III)-mediated ring opening of aziridines

Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.

Methods of Making Deuterium-Enriched N-acetylcysteine Amide (D-NACA) and (2R, 2R')-3,3'-Disulfanediyl BIS(2-Acetamidopropanamide) (DINACA) and Using D-NACA and DINACA to Treat Diseases Involving Oxidative Stress

The present invention includes pharmaceutical composition comprising (2R,2R′)-3,3′-disulfanediyl bis(2-acetamidopropanamide)(diNACA) or D3-N-acetyl cysteine amide, or a physiologically acceptable salt thereof, having a deuterium enrichment above the natural abundance of deuterium, and derivatives or solids thereof, and methods of using diNACA to treat eye diseases and other diseases associated with oxidative damage including, e.g., antivenom, beta-thallassemia, cataract, chronic obstructive pulmonary disease, macular degeneration, contrast-induced nephropathy, asthma, lung contusion, methamphetamine-induced oxidative stress, multiple sclerosis, Parkinson's disease, platelet apoptosis, Tardive dyskinesia, Alzheimer disease, HIV-1-associated dementia, mitochondrial diseases, myocardial myopathy, neurodegenerative diseases, pulmonary fibrosis, skin pigmentation, skin in need of rejuventation, antimicrobial infection, Friedreich's ataxia.

Method for Preparation of N-Acetyl Cysteine Amide and Derivatives Thereof

The present invention includes methods for making and isolating N-acetylcysteine amide, intermediates and derivatives thereof comprising: contacting cystine with an alcohol and a chlorinating reagent to form an organic solution containing L-cystine dimethylester dihydrochloride; combining dried or undried L-cystine dimethylester dihydrochloride with a triethylamine, an acetic anhydride, and an acetonitrile to form a di-N-acetylcystine dimethylester; mixing dried di-N-acetylcystine dimethylester with ammonium hydroxide to form a di-N-acetylcystine amide; and separating dried di-N-acetylcystine dimethylester into N-acetylcysteine amide with dithiothreitol, triethylamine and an alcohol.

COMPOUNDS AS L-CYSTINE CRYSTALLIZATION INHIBITORS AND USES THEREOF

A method of preventing or inhibiting L-cystine crystallization is disclosed, using the compounds of formula I: [in-line-formulae]R1a—[O]v-(-A-L-)m-A-[O]v—R1b [/in-line-formulae] wherein A, L, R1a, R1b, m, and v are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of conditions that are causally related to L-cystine crystallization, such as comprising (but not limited to) kidney stones.

Cysteine-based silver nanoparticles as dual colorimetric sensors for cations and anions

We report herein the synthesis of silver nanoparticles (Ag NPs), their characterization, and anion and cation sensing properties. Freshly prepared amide-triazole Ag NPs (3a-Ag NPs and 3b-Ag NPs) could detect fluoride and cations such as Hg2+ and Cd2+ in aqueous media with a color change from pink to brown. The cysteine-based Ag NPs 5b-Ag NPs showed a colorimetric response towards H2PO4-, whereas 6-Ag NPs showed a colorimetric response towards H2PO4- and HSO4- in aqueous media.