1069-29-0Relevant articles and documents
Cysteine-based silver nanoparticles as dual colorimetric sensors for cations and anions
Praveen Kumar,Kathuria, Lakshay,Haridas
, p. 8382 - 8389 (2016)
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.
Melt polycondensation approach for reduction degradable helical polyester based on l-cystine
Anantharaj, Santhanaraj,Jayakannan, Manickam
, p. 2864 - 2875 (2016)
Melt polycondensation approach is developed for new classes of reduction responsive disulfide containing functional polyesters based on l-cystine amino acid resources under solvent free process. l-Cystine was converted into multi-functional ester-urethane monomer and subjected to thermoselective transesterification at 120 °C with commercial diols in the presence of Ti(OBu)4 to produce polyesters with urethane side chains. The polymers were produced in moderate to high molecular weights and the polymers were found to be thermally stable up to 250 °C. The β-sheet hydrogen bonding interaction among the side chain urethane unit facilitated the self-assembly of the polyester into amyloid-like fibrils. The deprotection of urethane unit into amine functionality modified the polymers into water soluble cationic polyester spherical nanoparticles. The reduction degradation of disulfide bond was studied using DTT as a reducing agent and the high molecular weight polymers chains were found be chopped into low molecular weight oligomers. The cytotoxicity of cationic disulfide nanoparticle was studied in MCF-7 cells and they were found to be biocompatible and non-toxic to cells upto 50 μg/mL. The custom designed reduction degradable and highly biocompatible disulfide polyesters from l-cystine are useful for futuristic biomedical applications.
The trans opening of ethylene diamine tetra acetic acid bis anhydride (EDTAA) with cystine-di-OMe: One-step synthesis of bihelical systems Respectfully dedicated to Professor M.V. George on the occasion of his 85th birthday
Naini, Santhosh Reddy,Ranganathan, Subramania,Yadav, Jhillu Singh,Sarma,Ramakrishna,Nagaraj, Ramakrishnan,Premkumar, J. Richard,Sastry, G. Narahari
, p. 1132 - 1135 (2014)
The generation of a bihelical (figure of 8) motif has been illustrated by trans opening of EDTAA with l-cystine-di-OMe and d-penicillamine disulfide-di-OMe. In the former case the open cyclic system, arising by cis addition, was secured as a minor product.
Thiol Probes to Detect Electrophilic Natural Products Based on Their Mechanism of Action
Castro-Falcón, Gabriel,Hahn, Dongyup,Reimer, Daniela,Hughes, Chambers C.
, p. 2328 - 2336 (2016)
New methods are urgently needed to find novel natural products as structural leads for the development of new drugs against emerging diseases such as cancer and multiresistant bacterial infections. Here we introduce a reactivity-guided drug discovery approach for electrophilic natural products, a therapeutically relevant class of natural products that covalently modify their cellular targets, in crude extracts. Using carefully designed halogenated aromatic reagents, the process furnishes derivatives that are UV-active and highly conspicuous via mass spectrometry by virtue of an isotopically unique bromine or chlorine tag. In addition to the identification of high-value metabolites, the process facilitates the difficult task of structure elucidation by providing derivatives that are primed for X-ray crystallographic analysis. We show that a cysteine probe efficiently and chemoselectively labels enone-, β-lactam-, and β-lactone-based electrophilic natural products (parthenolide, andrographolide, wortmannin, penicillin G, salinosporamide), while a thiophenol probe preferentially labels epoxide-based electrophilic natural products (triptolide, epoxomicin, eponemycin, cyclomarin, salinamide). Using the optimized method, we were able to detect and isolate the epoxide-bearing natural product tirandalydigin from Salinispora and thereby link an orphan gene cluster to its gene product.
Kinetics and thermodynamics of oxidation mediated reaction in L-cysteine and its methyl and ethyl esters in dimethyl sulfoxide-d6 by NMR spectroscopy
Dougherty, Ryan J.,Singh, Jaideep,Krishnan
, p. 196 - 200 (2017)
L-Cysteine (L-Cys), L-Cysteine methyl ester (L-CysME) or L-Cysteine ethyl ester (L-CysEE), when dissolved in dimethyl sulfoxide, undergoes an oxidation process. This process is slow enough and leads to nuclear magnetic resonance (NMR) spectral changes that could be monitored in real time. The oxidation mediated transition is modeled as a pseudo-first order kinetics and the thermodynamic parameters are estimated using the Eyring's formulation. L-Cysteine and their esters are often used as biological models due to the remarkable thiol group that can be found in different oxidation states. This oxidation mediated transition is due to the combination of thiol oxidation to a disulfide followed by solvent-induced effects may be relevant in designing cysteine-based molecular models.
Oxidative Formation of Disulfide Bonds by a Chemiluminescent 1,2-Dioxetane under Mild Conditions
Sauer, Caroline S.,K?ckenberger, Johannes,Heinrich, Markus R.
supporting information, p. 9331 - 9338 (2020/08/14)
The oxidation of alkyl thiols to disulfides has been achieved under mild conditions using a chemiluminescent 1,2-dioxetane as a stoichiometric oxidant. Besides the mild and biocompatible reaction conditions, this approach offers the possibility to monitor the presence of thiols through oxidation and chemiluminescence of the remaining dioxetane.
Expressed Protein Ligation without Intein
Kratch, Kaci C.,Leeuwon, Sunshine Z.,Liu, Wenshe Ray,Morse, Jared S.,Qiao, Yuchen,Wang, Wesley Wei,Wang, Xiaoyan Aria,Xu, Shiqing,Yu, Ge
supporting information, p. 7047 - 7054 (2020/05/14)
Proteins with a functionalized C-terminus such as a C-terminal thioester are key to the synthesis of larger proteins via expressed protein ligation. They are usually made by recombinant fusion to intein. Although powerful, the intein fusion approach suffe
Preparation method of D-biotin intermediate
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Paragraph 0016, (2016/11/28)
The invention relates to a preparation method of a D-biotin intermediate.The preparation method includes the steps that L-cystine serves as a starting raw material, is subjected to methyl esterification and then reacts with benzyl isocyanate, intramolecul
Racemization-free synthesis of S-alkylated cysteines via thiol-ene reaction
Triola, Gemma,Brunsveld, Luc,Waldmann, Herbert
, p. 3646 - 3649 (2008/09/20)
(Chemical Equation Presented) Treatment of differently protected and unprotected cysteines with a variety of alkenes in the presence of a radical initiator (AIBN) afforded the corresponding S-alkylated cysteines in high yields and without racemization.
Process for S-Aryl cysteine
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Example 1, (2008/06/13)
The present invention provides methods for preparing S-aryl cysteines in enantiomeric excess of greater than about 96%. Specifically, the present invention provides enantioselective methods for preparing S-aryl cysteines starting from cystine, cysteine or
