- Biosynthetic selenoproteins with genetically-encoded photocaged selenocysteines
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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.
- Rakauskaite, Rasa,Urbanavi?iute, Giedre,Ruk?enaite, Audrone,Liutkevi?iute, Zita,Ju?kenas, Robertas,Masevi?ius, Viktoras,Klima?auskas, Saulius
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- CYSTINE DIAMIDE ANALOGS FOR CYSTINURIA
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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.
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Paragraph 0024; 0171-0172
(2021/06/22)
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- Redox-Driven Chiral Inversion of Water-Soluble Pillar[5]arene with l -Cystine Derivative in the Aqueous Medium
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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.
- Chen, Yuan,Sun, Baobao,Wang, Ranran,Shi, Conghao,Cheng, Ming,Jiang, Juli,Lin, Chen,Wang, Leyong
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supporting information
p. 7423 - 7427
(2021/10/01)
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- Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
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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.
- Alves, Diego,Sacramento, Manoela Do,Santi, Claudio,Schwab, Ricardo S.,Teixeira, Wystan K. O.,Yano De Albuquerque, Danilo
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supporting information
(2022/01/12)
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- Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity
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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.).
- Schlatzer, Thomas,Schr?der, Hilmar,Trobe, Melanie,Lembacher-Fadum, Christian,Stangl, Simon,Schl?gl, Christoph,Weber, Hansj?rg,Breinbauer, Rolf
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supporting information
p. 331 - 336
(2019/11/16)
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- Scalable synthesis of orthogonally protected β-methyllanthionines by indium(III)-mediated ring opening of aziridines
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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.
- Li, Ziran,Gentry, Zachary,Murphy, Brennan,Vannieuwenhze, Michael S.
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supporting information
p. 2200 - 2203
(2019/03/26)
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- 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
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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.
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Paragraph 0071; 0072
(2019/05/18)
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- Method for Preparation of N-Acetyl Cysteine Amide and Derivatives Thereof
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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.
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Paragraph 0049-0054
(2019/04/05)
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- COMPOUNDS AS L-CYSTINE CRYSTALLIZATION INHIBITORS AND USES THEREOF
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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.
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Paragraph 0315
(2018/11/21)
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- Cysteine-based silver nanoparticles as dual colorimetric sensors for cations and anions
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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.
- Praveen Kumar,Kathuria, Lakshay,Haridas
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supporting information
p. 8382 - 8389
(2016/10/11)
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- 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
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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.
- Naini, Santhosh Reddy,Ranganathan, Subramania,Yadav, Jhillu Singh,Sarma,Ramakrishna,Nagaraj, Ramakrishnan,Premkumar, J. Richard,Sastry, G. Narahari
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p. 1132 - 1135
(2014/02/14)
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- The exploration of Kemp's triacid (KTA) as the core for the synthesis of 3-fold symmetric 23-cyclophane, 22-cyclophane and novel linker directed designs
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For the first time, two units of KTA have been linked to three units of cyst-di-OMe. The reaction is noteworthy since it involves the formation of six amide bonds leading to a three-fold symmetric 23-cyclophane (3) harboring a cluster of three S-S bridges. The major product is a di-imide (4), arising from the interaction of a cystine NH with a neighbouring activated ester. A third reaction of tethering KTA with a single cyst-di-OMe unit afforded the flexible compound 6 and, with benzidine, the novel linker directed 7 with orthogonally disposed anchor modules.
- Naini, Santhosh Reddy,Ranganathan, Subramania,Yadav, Jhillu Singh,Ramakrishna,Gayatri,Sastry, G. Narahari,Roy, K. Basu,Shamala
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p. 5322 - 5328
(2014/01/23)
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- Organocatalytic visible light mediated synthesis of aryl sulfides
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Photo-sensitized synthesis of arylsulfides from arenediazonium salts in the presence of eosin Y has been developed. This protocol exhibits high functional group tolerance and a wide substrate scope and is an attractive alternative to the thermal reaction that involves explosive intermediates.
- Majek, Michal,Von Wangelin, Axel Jacobi
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supporting information
p. 5507 - 5509
(2013/06/27)
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- COMPOUNDS AS L-CYSTINE CRYSTALLIZATION INHIBITORS AND USES THEREOF
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A method of preventing or inhibiting L-cystine crystallization using the compounds of formula (I) is disclosed, wherein A, L, R1a, R1b, and m 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.
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Page/Page column 37; 38
(2011/06/19)
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- Reaction of N-acyloxy-N-alkoxyamides with biological thiol groups
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Mutagenic N-acyloxy-N-alkoxyamides 1 react with thiols by an SN2 process at nitrogen with displacement of carboxylate. They react with glutathione 4 in [D6]DMSO/D2O and methyl and ethyl esters of cysteine hydrochloride, 11 and 12, in [D4]methanol but the intermediate N-alkoxy-N-(alkylthio)amides undergo a rapid substitution reaction at sulfur by a second thiol molecule to give hydroxamic esters and disulfides. Arrhenius activation energies and entropies of activation obtained for a series of different N-benzyloxy-N-(4-substitutedbenzoyloxy)benzamides 13-17 were similar to those found for the SN2 reaction of the same series with N-methylaniline. Entropies of activation were strongly negative in keeping with polar separation and attendant solvation in the transition state, and in keeping with this, bimolecular reaction rate constants at 298K correlated with Hammett σ constants with a positive ρ-value of 1.1. The structure of model N-methoxy-N-(methylthio)acetamide has been computed at the B3LYP/6-31G(d) level and exhibits properties atypical of other anomeric amides with more electronegative atoms at nitrogen. Relative to N,N-bisoxyl substitution, the combination of a sulfur and an oxygen atom at the amide nitrogen results in a relatively small reduction in amide resonance.
- Glover, Stephen A.,Adams, Meredith
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body text
p. 443 - 453
(2011/10/09)
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- Triply bridged (1,3,5) cyclophanes from cystine and lanthionine linkers-a comparison
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The condensation of benzene 1,3,5-tricarbonylchloride with cystine-di-Me [H2N-CH(COOMe)-CH2-S-S-CH2-CH(COOMe)-NH 2] yielded triply bridged (1,3,5) cyclophane 1, which was shown by detailed spectral studies and molecular orbital calculations to have a D3 symmetry with conformationally identical linkers and a spherical topology. In sharp contrast, the (1,3,5) cyclophane 2 from the rarely studied lanthionine di-Me [H2N-CH(COOMe)-CH2-S-CH2-CH(COOMe)-NH 2], showed only a equatorial twofold symmetry. This work highlights the special properties of the -S-S- bridge in cystine, which makes it an exceptional synthon in nature and organic synthesis.
- Ranganathan,Venkateshwarlu,Babu,Reddy,Basha,Sarma,Vijay,Sastry
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experimental part
p. 3923 - 3929
(2010/07/05)
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- Synthesis and evaluation of new ω-borono-α-amino acids as rat liver arginase inhibitors
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Recent studies have demonstrated that arginase plays important roles in pathologies such as asthma or erectile dysfunctions. We have synthesized new ω-borono-α-amino acids that are analogues of the previously known arginase inhibitors S-(2-boronoethyl)-l-cysteine (BEC) and 2-amino-6- boronohexanoic acid (ABH) and evaluated them as inhibitors of purified rat liver arginase (RLA). In addition to the distance between the B(OH)2 and the α-amino acid functions, the position of the sulfur atom in the side chain also appears as a key determinant for the interaction with the active site of RLA. Furthermore, substitution of the alkyl side chain of BEC by methyl groups and conformational restriction of ABH by incorporation of its side chain in a phenyl ring led to inactive compounds. These results suggest that subtle interactions govern the affinity of inhibitors for the active site of RLA.
- Busnel, Olivier,Carreaux, Francois,Carboni, Bertrand,Pethe, Stephanie,Goff, Sandrine Vadon-Le,Mansuy, Daniel,Boucher, Jean-Luc
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p. 2373 - 2379
(2007/10/03)
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- Enantioselective cyclization of racemic supramolecular polymers
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Homochiral hydrogen-bonded cyclic assemblies are formed in dilute solutions of racemic supramolecular polymers based on the quadruple hydrogen bonding 2-ureido-4[1H]-pyrimidinone unit, as observed by 1H NMR and SEC experiments. Preorganization of the monomers and the combined binding strength of the eight hydrogen bonds result in a very high stability of the cyclic aggregates with pronounced selectivity between homochiral and heterochiral cyclic species, usually only observed in crystalline or liquid crystalline phases. Copyright
- Ten Cate, A. Tessa,Dankers, Patricia Y. W.,Kooijman, Huub,Spek, Anthony L.,Sijbesma, Rint P.,Meijer
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p. 6860 - 6861
(2007/10/03)
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- Defining the dimensions of the catalytic site of phospholipase A2 using amide substrate analogues
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Two series of phospholipid analogues, each containing a thioether function at the sn-1 position and an amide function at the sn-2 position, have been synthesized and evaluated as phospholipase A2 inhibitors. The first series of analogues contained a hexyl group (C-6) at the sn-1 position and various acyl groups at the sn-2 position, ranging from formyl to dodecanoyl (1-12 carbons). The second series contained an sn-1 hexadecyl group (C-16) and various sn-2 acyl groups from formyl to eicosanoyl (1-20 carbons). Hydrophobic interactions of the enzyme with the amide analogues were studied using several different substrate forms including monomers, micelles, and mixed micelles with Triton X-100. The C-6 amide analogues were used for the monomeric study while the C-16 analogues were used in the micellar studies. The inhibition studies with the monomeric amide analogues demonstrate that the sn-2 acyl chain is absolutely required for the binding of the analogue to the enzyme and that the catalytic site interacts with about the first 10 carbons of the sn-2 acyl chain. In addition, each methylene group of the sn-2 acyl chain from C5 to C10 provides about 665 cal/mol of binding energy. In contrast, the inhibition potency of the amide analogues in micellar states followed a quite different, more complex chain length dependency. The chain length of the sn-21 acyl group is much less important in the micellar systems than in the monomeric system, since the hydrophobic interactions between the sn-2 acyl chain and the enzyme are balanced by its interactions with the hydrophobic core of the micelle. The importance of double bonds in the sn-2 chain was also studied, but no correlation between the degree of unsaturation and the degree of inhibition was observed. These studies help delineate the mode of the interactions between enzyme and substrate.
- Yu, Lin,Dennis, Edward A.
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p. 8757 - 8762
(2007/10/02)
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