cas 3054-01-1, S-Benzyl-L-cysteine | Articles data

Articles about 3054-01-1Total 25 be found

Article title
Article abstract
Author
Journal number and time
Download

Expanding the Structural Diversity of Protein Building Blocks with Noncanonical Amino Acids Biosynthesized from Aromatic Thiols
Incorporation of structurally novel noncanonical amino acids (ncAAs) into proteins is valuable for both scientific and biomedical applications. To expand the structural diversity of available ncAAs and to reduce the burden of chemically synthesizing them, we have developed a general and simple biosynthetic method for genetically encoding novel ncAAs into recombinant proteins by feeding cells with economical commercially available or synthetically accessible aromatic thiols. We demonstrate that nearly 50 ncAAs with a diverse array of structures can be biosynthesized from these simple small-molecule precursors by hijacking the cysteine biosynthetic enzymes, and the resulting ncAAs can subsequently be incorporated into proteins via an expanded genetic code. Moreover, we demonstrate that bioorthogonal reactive groups such as aromatic azides and aromatic ketones can be incorporated into green fluorescent protein or a therapeutic antibody with high yields, allowing for subsequent chemical conjugation.
Wang, Yong,Chen, Xiaoxu,Cai, Wenkang,Tan, Linzhi,Yu, Yutong,Han, Boyang,Li, Yuxuan,Xie, Yuanzhe,Su, Yeyu,Luo, Xiaozhou,Liu, Tao
supporting information
p. 10040 - 10048
(2021/03/26)

Fluorovinylsulfones and -Sulfonates as Potent Covalent Reversible Inhibitors of the Trypanosomal Cysteine Protease Rhodesain: Structure-Activity Relationship, Inhibition Mechanism, Metabolism, and in Vivo Studies
Rhodesain is a major cysteine protease of Trypanosoma brucei rhodesiense, a pathogen causing Human African Trypanosomiasis, and a validated drug target. Recently, we reported the development of α-halovinylsulfones as a new class of covalent reversible cysteine protease inhibitors. Here, α-fluorovinylsulfones/-sulfonates were optimized for rhodesain based on molecular modeling approaches. 2d, the most potent and selective inhibitor in the series, shows a single-digit nanomolar affinity and high selectivity toward mammalian cathepsins B and L. Enzymatic dilution assays and MS experiments indicate that 2d is a slow-tight binder (Ki = 3 nM). Furthermore, the nonfluorinated 2d-(H) shows favorable metabolism and biodistribution by accumulation in mice brain tissue after intraperitoneal and oral administration. The highest antitrypanosomal activity was observed for inhibitors with an N-terminal 2,3-dihydrobenzo[b][1,4]dioxine group and a 4-Me-Phe residue in P2 (2e/4e) with nanomolar EC50 values (0.14/0.80 μM). The different mechanisms of reversible and irreversible inhibitors were explained using QM/MM calculations and MD simulations.
Jung, Sascha,Fuchs, Natalie,Johe, Patrick,Wagner, Annika,Diehl, Erika,Yuliani, Tri,Zimmer, Collin,Barthels, Fabian,Zimmermann, Robert A.,Klein, Philipp,Waigel, Waldemar,Meyr, Jessica,Opatz, Till,Tenzer, Stefan,Distler, Ute,R?der, Hans-Joachim,Kersten, Christian,Engels, Bernd,Hellmich, Ute A.,Klein, Jochen,Schirmeister, Tanja
p. 12322 - 12358
(2021/09/02)

Tanshinol and H2 S/NO Donor binding, preparation method thereof and application in pharmacy (by machine translation)
The invention belongs to the field of chemical pharmacy, and relates to active ingredient tanshinol and H in Chinese herbal medicine Salvia miltiorrhiza. 2 S/NO Donors and its preparation method and use in pharmacy, especially in the preparation of medicines for preventing and treating cardiovascular and cerebrovascular diseases and inflammation related diseases. To the invention, through in-vitro oxidative stress injury and inflammation model experiments, the results show that H is obviously inhibited. 2 O2 In vivo activity experiment results show that the conjugate is capable of remarkably inhibiting the release of inflammatory cytokines induced by LPS (LPS), reducing inflammation-induced mouse peritoneal macrophages, obviously inhibiting the release of inflammatory cytokines induced by LPS, and showing the result that the compound can be used for preparing drugs for preventing and treating cardiovascular and cerebrovascular diseases and inflammatory diseases. (by machine translation)
-
Paragraph 0113-0115

(2020/08/18)

Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents
A series of S-allyl-L-cysteine (SAC) with garlic acid conjugates as anti-inflammatory agents were designed and synthesized. Among the 40 tested compounds, SMU-8c exhibited the most potent inhibitory activity to Pam3CSK4-induced nitric oxide (NO) in RAW264.7 macrophages with IC50 of 22.54 ± 2.60 μM. The structure-activity relationship (SAR) study suggested that the esterified carboxyl group, carbon chain extension and methoxylation phenol hydroxy could improve the anti-inflammatory efficacy. Preliminary anti-inflammatory mechanism studies showed that SMU-8c significantly down-regulated the levels of Pam3CSK4 triggered TNF-α cytokine in human THP-1 cells, mouse RAW 264.7 macrophages, as well as in ex-vivo human peripheral blood mononuclear cells (PBMC) with no influence on cell viability. SMU-8c specifically blocked the Pam3CSK4 ignited secreted embryonic alkaline phosphatase (SEAP) signaling with no influence to Poly I:C or LPS triggered TLR3 or TLR4 signaling. Moreover, SMU-8c suppressed TLR2 in HEK-Blue hTLR2 cells and inhibited the formation of TLR1-TLR2, and TLR2-TLR6 complex in human PBMC. In summary, SMU-8c inhibited the TLR2 signaling pathway to down-regulate the inflammation cytokines, such as NO, SEAP and TNF-α, to realize its anti-inflammatory activity.
Bi, Jingjie,Wang, Wenqing,Du, Junxi,Chen, Kun,Cheng, Kui
p. 233 - 245
(2019/07/02)

Dynamic Kinetic Resolution for Asymmetric Synthesis of L-Noncanonical Amino Acids from D-Ser Using Tryptophan Synthase and Alanine Racemase
L-Ser is often used to synthesize some significant l-noncanonical α-amino acids(l-ncAAs), which are the prevalent intermediates and precursors for functional synthetic compounds. In this study, threonine aldolase from Escherichia coli k-12 MG1655 has been used to synthesize l-Ser. In contrast to the maximum catalytic capacity (20 g/L) for l-threonine aldolase(LTA), d-Ser was synthesized with high yield (240 g/L) from cheap Gly and paraformaldehyde using d-threonine aldolase (DTA) from Arthrobacter sp ATCC. In order to fully utilize d-Ser and expand the resource of l-Ser, a dynamic kinetic resolution system was constructed to convert d/dl-Ser to l-Ser through combining alanine racemase (Alr) from Bacillus subtilis with l-tryptophan synthase (TrpS) from Escherichia coli k-12 MG1655, and l-ncAAs including l-Trp and l-Cys derivatives were synthesized with excellent enantioselectivity and in high yields. The results indicated l-ncAAs could be efficiently synthesized from d-Ser using this original and green dynamic kinetic resolution system, and the reliable l-Ser resource has been established from simple and achiral substrates.
Yu, Jinhai,Li, Jing,Gao, Xia,Zeng, Shuiyun,Zhang, Hongjuan,Liu, Junzhong,Jiao, Qingcai
p. 6618 - 6625
(2019/11/03)

Facile Synthesis of S-Substituted L-Cysteines with Nano-sized Immobilized O-Acetylserine Sulfhydrylase
Many S-substituted l-cysteines are useful pharmaceutical intermediates but require a simple synthesis method. Here we developed enzymatic synthesis of several S-aryl-l-cysteines and S-benzyl-l-cysteine directly from O-acetylserine (OAS) with immobilized O-acetylserine sulfhydrylase CysM. Novel iron-oxide magnetic nanoparticles (MNPs) with cobalt-nitrilotriacetic acid function were prepared with a diameter of 80 nm in 75 % yield. Direct immobilization of His-tagged CysM in the cell-free extract on the MNPs via affinity attachment afforded stable nanobiocatalyst with 97 % enzyme loading efficiency and 93 % free enzyme activity. The immobilized enzyme catalyzed the biotransformation of benzylthiol and OAS to give S-benzyl-l-cysteine in 88 % yield. The nanobiocatalyst also demonstrated high recyclability, retaining 95 % productivity in the fifth cycle. The immobilized CysM accepts various arylthiols to react with OAS, giving rise to a new synthesis route of several S-substituted l-cysteines in 60–96 % yield.
Vahidi, Akbar K.,Wang, Zunsheng,Li, Zhi
p. 3671 - 3674
(2018/09/12)

Subtype-Specific Agonists for NMDA Receptor Glycine Binding Sites
A series of analogues based on serine as lead structure were designed, and their agonist activities were evaluated at recombinant NMDA receptor subtypes (GluN1/2A-D) using two-electrode voltage-clamp (TEVC) electrophysiology. Pronounced variation in subunit-selectivity, potency, and agonist efficacy was observed in a manner that was dependent on the GluN2 subunit in the NMDA receptor. In particular, compounds 15a and 16a are potent GluN2C-specific superagonists at the GluN1 subunit with agonist efficacies of 398% and 308% compared to glycine. This study demonstrates that subunit-selectivity among glycine site NMDA receptor agonists can be achieved and suggests that glycine-site agonists can be developed as pharmacological tool compounds to study GluN2C-specific effects in NMDA receptor-mediated neurotransmission.
Maolanon, Alex R.,Risgaard, Rune,Wang, Shuang-Yan,Snoep, Yoran,Papangelis, Athanasios,Yi, Feng,Holley, David,Barslund, Anne F.,Svenstrup, Niels,Hansen, Kasper B.,Clausen, Rasmus P.
p. 1681 - 1687
(2017/08/21)

A low-toxic artificial fluorescent glycoprotein can serve as an efficient cytoplasmic labeling in living cell
To maintain the virtue of good optical property and discard the dross of conventional fluorescent staining dyes, we provide a strategy for designing new fluorescent scaffolds. In this study, a novel fluorescent labeling glycoprotein (chitosan-poly-l-cysteine, CPC) was synthesized through graft copolymerization. CPC gives emission peak at 465470 nm when excited at 386 nm. The submicro-scale CPC microspheres could be localized and persisted specifically in the cytoplasm of living cells, with strong blue fluorescence. Moreover, CPC was highly resistant to photo bleaching, the fluorescence was remained stable for up to 72 h as the cells grew and developed. The glycoprotein CPC was bio-compatible and in zero grade cytotoxicity as quantified by MTT assay. The fluorescent labeling process with our newly designed glycoprotein CPC is exceptionally efficient.
Si, Jiangju,Liang, Dawei,Kong, Dan,Wu, Sufang,Yuan, Lan,Xiang, Yan,Jiang, Lei
supporting information
p. 211 - 214
(2015/02/19)

The synthesis and biological evaluation of novel Danshensu-cysteine analog conjugates as cardiovascular-protective agents
A series of novel amide and thioester conjugates between Danshensu and cysteine derivatives have been designed and synthesized based on the strategy of "medicinal chemical hybridization". Pharmacological evaluation indicated that the amide conjugates 3a/4a/17a and thioester conjugates 6a-d exhibited obvious protective effects on H2O2-induced human umbilical vein endothelial cells (HUVECs). Pretreated with these conjugates could increase glutathione (GSH) activity and decrease malondialdehyde (MDA) level. Further study on mechanism of compound 4a revealed that it was related to its mitochondrial-protective effect and regulation of apoptosis-related proteins expression (Bax, p53, PARP, caspase-3, caspase-9 and Bcl-2). These results indicate that these Danshensu-cysteine analog conjugates possess significant cardiovascular-protective effects and merit further investigation.
Jia, Yaoling,Zhou, Pengfei,Wang, Yang,Dong, Xiaoyi,Liu, Xinhua,Pan, Lilong,Xin, Hong,Zhu, Yi Zhun
p. 176 - 187,12
(2020/07/31)

Role of allyl group in the hydroxyl and peroxyl radical scavenging activity of S-allylcysteine
S-Allylcysteine (SAC) is the most abundant compound in aged garlic extracts, and its antioxidant properties have been demonstrated. It is known that SAC is able to scavenge different reactive species including hydroxyl radical (?OH), although its potential ability to scavenge peroxyl radical (ROO?) has not been explored. In this work the ability of SAC to scavenge ROO? was evaluated, as well as the role of the allyl group (-S-CH2-CH=CH2) in its free radical scavenging activity. Two derived compounds of SAC were prepared: S-benzylcysteine (SBC) and S-propylcysteine (SPC). Their abilities to scavenge ?OH and ROO? were measured. A computational analysis was performed to elucidate the mechanism by which these compounds scavenge ?OH and ROO?. SAC was able to scavenge ?OH and ROO?, in a concentration-dependent way. Such activity was significantly ameliorated when the allyl group was replaced by benzyl or propyl groups. It was shown for the first time that SAC is able to scavenge ROO?.
Maldonado, Perla D.,Alvarez-Idaboy, J. Raúl,Aguilar-González, Adriana,Lira-Rocha, Alfonso,Jung-Cook, Helgi,Medina-Campos, Omar Noel,Pedraza-Chaverrí, José,Galano, Annia
experimental part
p. 13408 - 13417
(2012/02/14)

Efficient S-alkylation of cysteine in the presence of 1,1,3,3- tetramethylguanidine
The synthesis of S-alkylated cysteine derivatives was carried out successfully in the presence of 1,1,3,3-tetramethylguanidine. Alkylation proceeded in high yields on unprotected amino acids and peptides containing a sulfhydryl group.
W?ostowski, Marek,Czarnocka, Sylwia,MacIejewski, Piotr
experimental part
p. 5977 - 5979
(2010/11/21)

Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula
(+)-Kalkitoxin, a metabolite of the marine cyanobacterium Lyngbya majuscula, was synthesized from (R)-2-methylbutyric acid, (R)-cysteine, and (3S, 4S, 6S)-3,4,6-trimethyl-8-(methylamino)octanoic acid. A key step in the synthesis was installation of the anti,anti methyl stereotriad by means of a tandem asymmetric conjugate addition of an organocopper species to an α,β-unsaturated N-acyl oxazolidin-2-one followed in situ by α-methylation of the resultant enolate. The thiazoline portion of kalkitoxin was assembled by titanium tetrachloride catalyzed cyclization of a vinyl substituted amido thiol.
White, James D.,Xu, Qing,Lee, Chang-Sun,Valeriote, Frederick A.
p. 2092 - 2102
(2007/10/03)

Total synthesis of (+)-kalkitoxin
The neurotoxic lipopeptide (+)-kalkitoxin was synthesized by a route which employed asymmetric organocopper conjugate addition followed by in situ enolate alkylation to install the anti,anti-1,2,4-trimethyl relationship of the toxin; the synthesis of kalkitoxin required sixteen steps and proceeded in 3% overall yield.
White, James D.,Lee, Chang-Sun,Xu, Qing
p. 2012 - 2013
(2007/10/03)

Initial intraorgan formation of mercapturic acid
The disposition of S-benzyl-glutathione (BSG) in male Wistar rats was evaluated by the HPLC method to examine whether the kidney and liver contributed independently to the biosynthesis of S-benzyl-N-acetylcysteine (BNAc), a mercapturic acid (Chart 1). After intravenous injection, BSG was rapidly transported in both the kidney and the liver at a ratio of about 7:3. Simultaneously, a large amount of BNAc was found in both the kidney and the liver. In the kidney, S-benzyl-cysteine (BCys) reached a maximum concentration (Cmax) at 2 min after BSG injection, whereas BNAc reached Cmax within 3 to 5 min. The generation of BNAc was also observed in the liver. While renal BNAc reached Cmax within 3 to 5 min, hepatic BNAc reached Cmax around 5 min after BSG injection. Moreover, the elimination half-life of the BNAc after intravenous injection of the BSG was equivalent to that observed after intravenous injection of the BNAc itself. These results demonstrate that the kidney contributes to the initial intraorgan generation of BNAc and that this mercapturic acid is also synthesized in the liver and preferentially excreted into urine.
Sano,Ikegami,Uesugi
p. 1324 - 1328
(2007/10/03)

Acylase-catalyzed deacetylation of haloalkene-derived mercapturates
Mercapturates (S-substituted N-acetyl-L-cysteines) are terminal metabolites formed by the glutathione-dependent metabolism of electrophilic xenobiotics, including haloalkenes. Acylases catalyze the hydrolysis of N- acyl-L-amino acids, including many xenobiotic-derived mercapturates, to give fatty acids and amino acids as products. Although several acylases have been identified, the acylases that catalyze the deacetylation of the haloalkene- derived mercapturates have not been identified and characterized. Acylase I catalyzes the deacetylation of some haloalkene-derived mercapturates, including S-(1,1,2,2-tetrafluoroethyl)-N-acetyl-L-cysteine, S-(2-chloro- 1,1,2-trifluoroethyl)-N-acetyl-L-cysteine, and S-(2-bromo-1,1,2- trifluoroethyl)-N-acetyl-L-cysteine [Uttamsingh, V., et al. (1998) Chem. Res. Toxicol. 11, 800-809]. In the studies presented here, we identified a rat kidney acylase that catalyzed the hydrolysis of the haloalkene-derived mercapturates S-(1,2-dichlorovinyl)-N-acetyl-L-cysteine, S-(1,2,3,4,4- pentachloro-1,3-butadienyl)-N-acetyl-L-cysteine, and S-(2,2-dibromo-1,1- difluoroethyl)-N-acetyl-L-cysteine. The substrate selectivity and amino acid sequence of the purified rat kidney acylase were studied. Although the sequence of the purified rat kidney acylase was somewhat identical with that of aspartoacylase, it did not catalyze the hydrolysis of N-acetyl-L- aspartate.
Uttamsingh, Vinita,Anders
p. 937 - 942
(2007/10/03)

Peptide Synthesis in Aqueous Solution. V. Properties and Reactivities of (p-Hydroxyphenyl)benzylmethylsulfonium Salts for Direct Benzyl Esterification of N-Acylpeptides
Some (p-hydroxyphenyl)benzylmethylsulfonium salts were prepared. These compounds generated a benzyl cation and converted not only N-acylamino acids but also N-acylpeptides into their corresponding benzyl esters without causing the racemization.
Nakata, Takashi,Nakatani, Masaru,Takahashi, Masatoshi,Okai, Jiro,Kawaoka, Yoshiaki,Kouge, Katsushige,Okai, Hideo
p. 1099 - 1106
(2007/10/03)

Total synthesis of nosiheptide. Synthesis of thiazole fragments
The preparation of three new thiazole derivatives from natural products is described, as well as improvements in the synthesis of ethyl 2-aminomethyl-4-thiazolecarboxylate.
Koerber-Ple,Massiot
p. 1309 - 1315
(2007/10/03)

Two new procedures for the introduction of benzyl-type protecting groups for thiols
Two new methods for the benzylation of thiols are described: a) direct-S- alkylation with para-substituted benzylic cations; and b) reductive S- alkylations of 2-aminothiols. Both methods provide efficient routes for the introduction of benzyl-type protecting groups in high yields.
Richter, Lutz S.,Marsters Jr., James C.,Gadek, Thomas R.
p. 1631 - 1634
(2007/10/02)

Versatile Synthesis of Stereospecifically Labelled D-Amino Acids via Labelled Aziridines - Preparation of (2R,3S)-- and (2R,3R)--Serine; (2S,2'S,3S,3'S)-- and (2S,2'S,3R,3'R)--Cystine; and (2S,3S)- and (2S,3R)--β-Chloroalanine
Stereospecifically β-labelled protected 2-carboxyaziridines 2, with the stereochemistry of a D-amino acid at C-2, have been prepared by a chemicoenzymic synthesis.Preparation of the labelled malates 5, by hydration of fumaric acid using the enzyme fumarase or by amination with aspartase followed by nitrosation, was followed by conversion into the isoserines 3, by a process involving Curtius rearrangement with retention of stereochemistry at the chirally labelled primary centre.Protection and ring closure gave the aziridines 2, which, on ring opening with the appropriate nucleophiles and deprotection, gave stereospecifically labelled samples of D-serine 16, D-cystine 20 and β-chloro-D-alanine 22.
Axelsson, B. Svante,O'Toole, Kevin J.,Spencer, Philip A.,Young, Douglas W.
p. 807 - 816
(2007/10/02)

SYNTHESIS OF ETHYL N-CARBOBENZOXYTYROSYL-S-BENZYLCYSTEINYLGLYCINATE
-
Dymicky, Michael,Byler, D. Michael
p. 93 - 102
(2007/10/03)

S-carboxymethylcysteine synthase from Escherichia coli
-
Kumagai,Suzuki,Shigematsu,Tochikura
p. 2481 - 2487
(2007/10/02)

ASYMMERTIC SYNTHESIS OF Β-SUBSTITUTED α-AMINO ACIDS VIA A CHIRAL Ni(II) COMPLEX OF DEHYDROALANINE
An efficient approach to the asymmetric synthesis of β-substituted (S)-alanines is describen.The chiral Ni(II) complex of a Schiff base derived from (S)-o-N-(N-benzylpropyl)aminobenzophenone (BBP) and glycine was treated with formaldehyde and sodium methoxide to give a corresponding (R)-serine complex which, in turn, was converted to the chiral Ni(II) dehydroalanine complex.Michael type base catalyzed addition of nucleophiles (including MeOH, Me2NH, PhCH2NH2, imidazole, PhSH, PhCH2SH,, malonic ester and benzylmagnesium chloride) produced a mixture of diastereoisomeric complexes with a 70-90percent excess of S,S (or L,L) isomers over the S,R (or L,D) ones.The cleavage of pure diastereoisomers with aqueous HCl gave, in good yields, β-substituted (S) (or L)-alanines and regenerated the chiral auxiliary (BBP).
Belokon, , Yuri N.,Sagyan, Ashot S.,Djamgaryan, Silva M.,Bakhmutov, Vladimir I.,Belikov, Vasili M.
p. 5507 - 5514
(2007/10/02)

Synthesis and evaluation of N-alkanoyl-S-benzyl-L-cysteinylglutamic acid esters as glyoxalase I inhibitors and anticancer agents
Esters of several glutathione analogues have been synthesized in which the glycine moiety was replaced by straight-chain fatty acids and the mercapto group was benzylated. Two of the derivatives (sufficiently water-soluble for the assay) were found to inhibit glyoxalase I to a greater extent than did S-methylglutathione. The two glyoxalase I inhibitors did not inhibit P388 lymphocytic leukemia in mice, however.
Foye,Jan
p. 559 - 561
(2007/10/02)

Enzymatic Synthesis of S-Substituted L-Cysteines with Tryptophan Synthase of Escherichia coli
The α2β2 comlex of tryptophan syntase from Escherichia coli catalyzes β-replacement reactions of L-serine and its derivatives (e.g., β-chloro-L-alanine and O-methyl-DL-serine) with various alkanethiols.The products from thiobenzyl alcohol and ethanethiol were isolated to demonstrate the enzymatic synthesis of the corresponding S-substituted L-cysteines.Reactivities of various S-substituent donors were examined, and thiols such as thiobenzyl alcohol, 1-propanethiol and 1-butanethiol were found to be much more efficient substituent donors than the physiological substrate, indole.In addition, tryptophan synthase catalyzes β-replacement reactions of L-threonine with thiols to form the corresponding S-substituted β-methylcysteines, which are also produced by β-addition reactions of L-vinylglycine with thiols.These enzymatic reactions facilitate the synthesis of various sulfur-containing amino acids.
Esaki, Nobuyoshi,Tanaka, Hidehiko,Miles, Edith Wilson,Soda, Kenji
p. 2861 - 2864
(2007/10/02)