6968-11-2

Basic information

• Product Name: N,N'-Bis(benzyloxycarbonyl)-L-cystine
• Synonyms: (CBZ-CYS-OH)2;DI-CBZ-L-CYST;DI-CBZ-L-CYSTINE;DI-N-CBZ-L-CYSTINE;DI-N-BENZYLOXYCARBONYL-L-CYSTINE;(DI-Z-CYS-OH)2;DI-Z-L-CYSTINE;N-ALPHA-N-ALPHA-BIS-Z-L-CYSTINE
• CAS NO: 6968-11-2
• Molecular Formula: C₂₂H₂₄N₂O₈S₂
• Molecular Weight: 508.56
• EINECS: 230-181-3
• Product Categories: Amino Acid Derivatives;Cysteine [Cys, C];Z-Amino Acids and Derivatives;Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Z-Amino acid series
• Mol File: 6968-11-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 118-122 °C (dec.)
• Boiling Point: 766.1 °C at 760 mmHg
• Flash Point: 417.1 °C
• Appearance: White/Powder
• Density: 1.422 g/cm³
• Vapor Pressure: 1.11E-24mmHg at 25°C
• Refractive Index: -91 ° (C=8.8, AcOH)
• Storage Temp.: Store at RT.
• Solubility: almost transparency in Methanol
• PKA: 3.15±0.10(Predicted)
• CAS DataBase Reference: N,N'-Bis(benzyloxycarbonyl)-L-cystine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Bis(benzyloxycarbonyl)-L-cystine(6968-11-2)
• EPA Substance Registry System: N,N'-Bis(benzyloxycarbonyl)-L-cystine(6968-11-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6968-11-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N,N''-Dibenzyloxycarbonyl-L-cystine

InChI:InChI=1/C22H24N2O8S2/c25-19(26)17(23-21(29)31-11-15-7-3-1-4-8-15)13-33-34-14-18(20(27)28)24-22(30)32-12-16-9-5-2-6-10-16/h1-10,17-18H,11-14H2,(H,23,29)(H,24,30)(H,25,26)(H,27,28)/t17-,18-/m0/s1

Upstream product

• 56-89-3 L-cystine 
• 501-53-1 benzyl chloroformate 
• 96289-13-3 N-benzyloxycarbonyl-L-cysteine 
• 91285-94-8 O-benzyl S-(pyridin-2-yl)carbonothioate 
• 96452-48-1 benzyl pyridin-2-yl carbonate 
• 26311-04-6 N-benzyloxycarbonyl-S-trityl-L-cysteine 
• 100-51-6 benzyl alcohol 
• 2450-71-7 Propargylamine 
• 928-90-5 5-hexyl-1-ol 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 3693-95-6 N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester 
• 96289-13-3 N-benzyloxycarbonyl-L-cysteine 
• 2790-85-4 bis-N-carbobenzyloxycysteinyl-bis-glycine diethyl ester 
• 103153-83-9 L-cystine-dianilide 
• 40470-28-8 N.N'-bis-benzyloxycarbonyl-L-cystyl dichloride 
• 104098-35-3 N,N'-bis-benzyloxycarbonyl-L-cystine bis-(2-hydroxy-ethylamide) 
• 116973-09-2 N,N'-bis-benzyloxycarbonyl-L-cystine di-p-toluidide 
• 103401-69-0 N,N'-bis-benzyloxycarbonyl-L-cystine bis-(N'-benzoyl-hydrazide) 
• 104511-01-5 N,N'-bis-benzyloxycarbonyl-L-cystine di-p-anisidide 
• 116151-93-0 N,N'-bis-benzyloxycarbonyl-L-cystine bis-[N'-(4-nitro-benzoyl)-hydrazide] 
• 103331-42-6 N,N'-bis-benzyloxycarbonyl-L-cystine-bis-(N'-isonicotinoyl-hydrazide) 
• 119534-36-0 S,S'-dibenzyl-N,N'-bis-(N,N'-bis-benzyloxycarbonyl-L-cystyl)-bis-L-cysteine 
• 64957-09-1 N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester 
• 104622-46-0 N,N'-bis-benzyloxycarbonyl-L-cystine bis-[2]naphthylamide 

Relevant articles and documents

Highly Selective Sub-Nanomolar Cathepsin S Inhibitors by Merging Fragment Binders with Nitrile Inhibitors

Pharmacological inhibition of cathepsin S (CatS) allows for a specific modulation of the adaptive immune system and many major diseases. Here, we used NMR fragment screening and crystal structure-aided merging to synthesize novel, highly selective CatS inhibitors with picomolar enzymatic Ki values and nanomolar functional activity in human Raji cells. Noncovalent fragment hits revealed binding hotspots, while the covalent inhibitor structure-activity relationship enabled efficient potency optimization.

Application of a novel small scale UV LED photochemical batch reactor for the thiol-yne reaction

The application of a novel small scale UV LED photochemical batch reactor for the thiol-yne click reaction was investigated. Optimization of the reaction conditions yielded high conversions. Finally, the methodology could be successfully expanded to the one pot insertion of functionalized alkynes into the disulfide bond of a cysteine derivative.

Acyl transfer from carboxylate, carbonate, and thiocarbonate esters to enzymatic and nonenzymatic thiolates

Transglutaminases (EC 2.3.2.13) (TGases) catalyze calcium-dependent acyl transfer reactions between peptide-bound glutamine residues as acyl donors and peptide-bound lysine residues as acyl acceptors, resulting in the formation of intermolecular ε-(γ-glutamyl)lysine crosslinks. The mechanistic details of its "ping-pong" transamidation reaction remain unknown. In particular, few studies have been published probing the nucleophilicity of TGase using acyl-donor substrates of varied electrophilicity. Herein we report the synthesis of activated esters of carbonates, carbamates, and thiocarbonates and their reactions with simple thiols, as a nonenzymatic point of reference, and with the catalytic cysteine residue of guinea pig liver TGase. Our kinetic results show that the simple substitution of a side chain methylene unit by oxygen or sulphur had a surprising effect on both substrate affinity and acylation reactivity. Furthermore, they provide unexpected insight into the importance of a side chain heteroatom for conferring affinity for tissue TGase as well as revealing an interesting class of irreversible inhibitors.