- Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity
-
Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that thel-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range ofN-acyl-amino acid substrates. This activity was revealed by1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used to probe the subtle structural selectivity of the biocatalyst using a substrate that could adopt different rotameric conformations.
- De Cesare, Silvia,McKenna, Catherine A.,Mulholland, Nicholas,Murray, Lorna,Bella, Juraj,Campopiano, Dominic J.
-
supporting information
p. 4904 - 4909
(2021/06/16)
-
- KCNT1 INHIBITORS AND METHODS OF USE
-
The present invention is directed to, in part, compounds and compositions useful for preventing and/or treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene (e.g., KCNT1). Methods of treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene such as KCNT1 are also provided herein.
- -
-
Paragraph 000628
(2020/11/23)
-
- Asymmetric synthesis of (S,R)- and (R,R)-methiin stereoisomers
-
An asymmetric synthesis of (+)- and (–)-methiine (S-methyl-(R)-cysteine sulfoxide) diastereomers has been developed. These natural sulfur compounds were isolated from a variety of Brassica vegetables. As the starting compound, (R)-cysteine was used, which was methylated to form (R)-S-methylcysteine. Then the oxidation of S-methylcysteine with tert-butyl hydroperoxide catalyzed by the chiral tetra(isopropylate)titanium/(S)- or (R)-Binol complex led to the formation of (1 R,2S)-(+)- or (1 R,2R)-(–)-methiin stereomers.
- Kolodiazhna, Anastasy О.,Skliarov, Аleksei I.,Slastennikova, Alena A.,Kolodiazhnyi, Oleg I.
-
p. 713 - 717
(2020/05/11)
-
- Symmetric benzidine derivatives as anti-HCV agents: Insight into the nature, stereochemistry of the capping amino acid and the size of the terminal capping carbamates
-
Novel symmetric molecules, bearing a benzidine prolinamide core, two terminal carbamate caps of variable sizes and nature, including natural and unnatural amino acids were developed. Several terminal N-carbamate substituents of the core structure, ranging from linear methyl, ethyl and butyl groups to branching isobutyl group; and an aromatic substituent were also synthesized. Series 1 has hydrophobic AA residues, namely S and R phenylglycine and a terminal carbamate capping group, whereas Series 2 bears sulphur containing amino acids, specifically S and R methionine and the natural R methylcysteine. The novel compounds were tested for their inhibitory activity (EC50) and their cytotoxicity (CC50), using an HCV 1b (Con1) reporter replicon cell line. Compound 4 with the unnatural capping residue, bearing D-Phenylglycine amino acid residue and N-isobutyloxycarbonyl capping group, was the most active within the two series, with EC50 = 0.0067 nM. Moreover, it showed high SI50 > 14788524 and was not cytotoxic at the highest tested concentration (100 μΜ), indicating its safety profile. Compound 4 also inhibited HCV genotypes 2a, 3a and 4a. Compared to the clinically approved NS5A inhibitor Daclatasvir, compound 4 shows higher activity against genotypes 1b and 3a, as well as improved safety profile.
- Abadi, Ashraf H.,Abdel Karim, Shereen E.,Abdel-Halim, Mohammad,Ahmed, Nermin S.,Frakolaki, Efseveia,Vassilaki, Niki,Youssef, Youssef H.,Zoidis, Grigoris
-
-
- Composition for promoting differentiation of skin keratinocyte comprising a SAC derivatives or a SMC derivatives
-
The present invention relates to a composition for promoting keratinocyte differentiation. More specifically, SAC derivative or SMC derivatives as an active ingredient promotes differentiation of keratinocytes to promote skin keratinocyte differentiation, has excellent anti-wrinkling effect, skin barrier recovery effect, and is applicable to pharmaceutical, cosmetic, soap, body, shampoo and pack.
- -
-
Paragraph 0057-0060; 0062-0064; 0111-0114; 0116-0118; 0161
(2021/02/02)
-
- Discovery of a novel dipeptidyl boronic acid proteasome inhibitor for the treatment of multiple myeloma and triple-negative breast cancer
-
A series of novel dipeptidyl boronic acid compounds were designed, synthesized and biologically investigated for the inhibition of the β5 subunit of 20S proteasome and several compounds showed high activities with IC50 values of less than 10 nM. Some of these compounds potently inhibited the multiple myeloma (MM) cancer cell lines with IC50 values of less than 10 nM. It was reported that the inhibition of both β2 and β5 subunits strongly increased the cytotoxicity of proteasome inhibitors in solid tumor cells, so some of the compounds were evaluated for the inhibition of the β2 subunit and the solid tumor triple-negative breast cancer cell line MDA-MB-231. The results showed that three compounds were active for both the β2 subunit and the triple-negative breast cancer cell line MDA-MB-231. The in vivo pharmacokinetic results showed that compound 8t had good biological parameters for both ig and iv administrations. An in vivo pharmacodynamic experiment showed that compound 8t inhibited the β5 subunit in whole blood more greatly than the marketed MLN9708 with the same dose at different time periods. A pathological analysis indicated that the injection of compound 8t in the tumor of a triple-negative breast cancer xenograft mice model led to tumor cell necrosis, nucleus condensation, deep staining, cell fragmentation, dissolution and neutrophil infiltration compared with the control group. The data in hand showed that compound 8t might be an effective candidate for the treatment of both MM and triple-negative breast cancer.
- Lei, Meng,Feng, Huayun,Bai, Enhe,Zhou, Hui,Wang, Jia,Qin, Yanru,Zhang, Haoyang,Wang, Xueyuan,Liu, Zhaogang,Hai, Ou,Liu, Jia,Zhu, Yongqiang
-
p. 683 - 691
(2019/01/24)
-
- Synthesis and application of peptide borate compounds
-
The invention belongs to the field of drug synthesis, and specifically relates to a series of novel peptide borate compounds or pharmaceutical salts thereof, and a preparation method and pharmaceutical application thereof. The structure of the peptide borate compounds or the pharmaceutical salts thereof is as shown in a formula I which is described in the specification. The compounds of the invention can be used for preparing proteasome inhibitors, and thus can be further used for treating solid tumors and blood tumors.
- -
-
Paragraph 0142; 0157-0161
(2019/12/25)
-
- A step-by-step crystallization for preparing thio alkyl/alkenyl cysteine sulfoxide method
-
The invention discloses a method for preparing thioalkyl/alkenyl cysteine sulfoxide by fractional crystallization, belonging to the technical field of compound preparation. The method comprises the following steps: adding cysteine or cysteine salts, a sodium hydroxide solution and an R group (alkyl or alkenyl)-derived material into absolute ethanol in sequence for reaction to synthesize coarse ACSs, re-crystallizing ACSs, purifying, oxidizing to form ACSOs, and fractionally crystallizing to obtain natural dextrorotatory ACSOs, wherein the R group-derived material is replaced to synthesize different types of ACSOs in allium; enantiomers in racemes are separated by adopting the fractional crystallization method to obtain natural dextrorotatory ACSOs with optical activity. Compared with a conventional extraction method, the method has the characteristics that the yield and the purity are high, a conventional complicated extraction process is avoided, the product has the optical activity, and the physical property is close to that of natural extract; the product is used in the fields of health products, pharmaceuticals and the like, the effects of resisting bacteria and cancers, reducing blood fat and the like of ACSOs are brought into play, or the product serves as an intermediate such as an active ingredient-diallyl thiosulfinate for synthesizing allium.
- -
-
Paragraph 0045 - 0047
(2017/05/26)
-
- Engineered Citrobacter freundii methionine γ-lyase effectively produces antimicrobial thiosulfinates
-
Antimicrobial activity of thiosulfinates in situ produced by mixtures of Citrobacter freundii methionine γ-lyase (MGL) with new substrates, L-methionine and S-(alkyl/allyl)-L-cysteine sulfoxides has been recently demonstrated (Anufrieva et?al., 2015). This opens a way to the rational design of a new biotechnologically relevant antimicrobial drug producer. To increase the efficiency of the enzyme toward sulfoxides, the mutant forms of MGL, with the replacements of active site cysteine 115 with alanine (C115A MGL) and histidine (C115H MGL) were obtained. The replacement of cysteine 115 by histidine results in the loss of activity of the mutant enzyme in the γ-elimination reaction of physiological substrate, whereas the activity in the β-elimination reaction of characteristic substrates persists. However, the catalytic efficiency of C115H MGL in the β-elimination reaction of S-substituted L-cysteine sulfoxides is increased by about an order of magnitude compared to the wild type MGL. The antibacterial activity of C115H MGL mixtures with a number of sulfoxides was assessed against Gram-positive and Gram-negative bacteria. The bacteriostatic effect was more pronounced against Gram-positive than against Gram-negative bacteria, while antibacterial potential proved to be quite similar. Thus, the mutant enzyme C115H MGL is an effective catalyst, in particular, for decomposition of sulfoxides and the pharmacological couples of the mutant form with sulfoxides might be new antimicrobial agents.
- Morozova, Elena A.,Kulikova, Vitalia V.,Rodionov, Alexei N.,Revtovich, Svetlana V.,Anufrieva, Natalya V.,Demidkina, Tatyana V.
-
-
- Dipeptide boric acid composed of carboxylic acid and alpha-amino acid as well as ester compound thereof, and preparation method and application of dipeptide boric acid and ester compound thereof
-
The invention belongs to the field of drug synthesis and in particular relates to a series of novel peptide boric acids as well as an ester compound or pharmaceutical salt thereof, and a preparation method and application of the peptide boric acids as well as the ester compound or pharmaceutical salt thereof in pharmacodynamics. A structure of the peptide boric acid and the ester compound or pharmaceutical salt thereof is shown in a formula I (described in the specification). The compound provided by the invention can be used for preparing a proteasome inhibitor and can further be used for treating solid tumours and blood tumours, wherein the solid tumours are selected from non-small cell lung cancer, small cell lung cancer, lung adenocarcinoma, lung squamous carcinoma, pancreatic cancer, breast cancer, prostate cancer, liver cancer, skin cancer, epithelial cell cancer, gastrointestinal stromal tumor, nasopharynx cancer and leukemia; and the blood tumours are selected from multiple myeloma, mantle cell lymphoma and histiocytic lymphoma.
- -
-
Paragraph 0137; 0138; 0139; 0140
(2016/12/01)
-
- Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers
-
In the search for new ligands for the Ullmann diaryl ether synthesis, permitting the coupling of electron-rich aryl bromides at relatively low temperatures, 56 structurally diverse multidentate ligands were screened in a model system that uses copper iodide in acetonitrile with potassium phosphate as the base. The ligands differed largely in their performance, but no privileged structural class could be identified.
- Otto, Nicola,Opatz, Till
-
supporting information; experimental part
p. 1105 - 1111
(2012/09/07)
-
- 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)
-
- Ionic liquids as performance additives for electroenzymatic syntheses
-
Electroenzymatic syntheses combine oxidoreductase-catalysed reactions with electrochemical reactant supply. The use of ionic liquids as performance additives can contribute to overcoming existing limitations of these syntheses. Here, we report on the infl
- Kohlmann, Christina,Greiner, Lasse,Leitner, Walter,Wandrey, Christian,Luetz, Stephan
-
experimental part
p. 11692 - 11700
(2010/04/29)
-
- Cysteine based novel noncompetitive inhibitors of urease(s)-Distinctive inhibition susceptibility of microbial and plant ureases
-
Based on the catalysis mechanism of urease, a homologous series of 10 cysteine derivatives (CysDs) was designed and synthesized, and their inhibitory activities were evaluated for microbial ureases (Bacillus pasteurii, BPU, and Proteus mirabilis, PMU) and for a plant urease [jack bean (Cavavalia ensiformis), JBU]. As already described, thiol-compounds might inhibit urease activity by chelating the nickel atoms involved in the catalysis process. In contrast to cysteine, which has been reported to be a very weak urease inhibitor, we verified a potential inhibitory activity of these CysDs. The kinetic data demonstrate that thiol derivatives are more effective than the respective thioether derivatives. Besides, thiol-CysDs had a reduced activity in acidic pH (5.0). Lineweaver-Burk plots indicated that the nature of inhibition was of noncompetitive type for all 10 compounds, with the minimum Ki value of 2 μM for N,N-dimethyl l-cysteine. It is proposed that these classes of compounds are more potent inhibitors of the bacterial ureases, compared with the plant-originated urease. Since microbial urease is directly involved in the infection process of many pathological organisms, this work demonstrates that thiol-CysDs represent a class of new potential urease inhibitors.
- Amtul, Zareen,Kausar, Naheed,Follmer, Cristian,Rozmahel, Richard F.,Atta-Ur-Rahman,Kazmi, Syed Arif,Shekhani, Mohammed Saleh,Eriksen, Jason L.,Khan, Khalid M.,Choudhary, Mohammad Iqbal
-
p. 6737 - 6744
(2007/10/03)
-
- Palatability of aquaculture feed
-
A method for enhancing the palatability of aquaculture food, the method comprising treating the food with a compound of Formula I: wherein R1, R2, R3, and n are as defined herein, are disclosed.
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-
-
- N-Salicylideneamino acidato complexes of oxovanadium(IV). the cysteine and penicillamine complexes
-
Oxovanadium(iv) complexes with ligands derived from the reaction of salicylaldehyde with L-cysteine and with D- and D,L-penicillamine are prepared. The compounds are characterised by elemental analysis, spectroscopy (UV-VIS, CD, EPR), TG, DSC and magnetic susceptibility measurements (9-295 K). We discuss several aspects related to the structure of these complexes in the solid state and in solution; in particular, the possibility of forming thiazolidine complexes, and their comparison with the characterised complexes is studied by molecular mechanics and density functional theory calculations. The solution structures depend on pH and solvent, and while with L-Cys the spectroscopic results show trends similar to those of the L-Ala and L-Ser systems up to ca. pH 8-9, where thiolate coordination starts being detected, the penicillamine system is quite distinct, namely thiolate coordination occurs for pH > 6.5. In the presence of salicylaldehyde and VIVO the desulfydration of cysteine proceeds rapidly, but no similar reaction occurs with penicillamine, although its decomposition is also activated. The DFT calculations do not indicate any energetic basis for this distinct reactivity, which possibly results from different complexes present in the Cys and Pen systems. In the cysteine system, the N-salicylidene dehydroalanine-VIVO complex V is believed to form in an intermediate stage of the desulfydration. Further, addition of several nucleophiles to the cysteine reaction mixtures produce amino acid derivatives by a Michael-type base-catalysed addition, a result compatible with the formation of V. The products of these reactions were analysed by TLC and HPLC, and in some cases isolated.
- Pessoa, Joao Costa,Calhorda, Maria J.,Cavaco, Isabel,Costa, Paulo J.,Correia, Isabel,Costa, Dina,Vilas-Boas, Luis F.,Felix, Vitor,Gillard, Robert D.,Henriques, Rui T.,Wiggins, Robert
-
p. 2855 - 2866
(2007/10/03)
-
- CARBOXAMIDE DERIVATIVES AND THEIR USE AS FACTOR XA INHIBITORS
-
The invention relates to the novel compounds of formula (I), wherein R1, D, X, W, Y and T are defined as in claim 1, for example (II). The novel compounds inhibit coagulation factor Xa and can be used for the prophylaxis and/or therapy of thromboembolic diseases and for the treatment of tumors.
- -
-
Page/Page column 32-33
(2008/06/13)
-
- Process for the preparation of S-alkylcysteines
-
A process for the preparation of S-alkylcysteines of formula wherein R is a lower or branched C1-C4 alkyl group; by S-alkylation of cysteines with dialkylcarbonates.
- -
-
-
- Beauveria bassiana ATCC 7159 contains an L-specific α-amino acid benzamidase
-
Biotransformation of a series of racemic N-benzoyl α-amino acids by the fungus Beauveria bassiana ATCC 7159 results in isolation of the corresponding D-amino acid benzamides in high enantiomeric purity and yield.
- Holland, Herbert L.,Andreana, Peter R.,Salehzadeh-Asl, Reza,Van Vliet, Aaron,Ihasz, Nancy J.,Brown, Frances M.
-
p. 667 - 672
(2007/10/03)
-
- Acylase I-catalyzed deacetylation of N-acetyl-L-cysteine and S-alkyl-N- acetyl-L-cysteines
-
The aminoacylase that catalyzes the hydrolysis of N-acetyl-L-cysteine (NAC) was identified as acylase I after purification by column chromatography and electrophoretic analysis. Rat kidney cytosol was fractionated by ammonium sulfate precipitation, and the proteins were separated by ion-exchange column chromatography, gel-filtration column chromatography, and hydrophobic interaction column chromatography. Acylase activity with NAC and N-acetyl-L- methionine (NAM), a known substrate for acylase I, as substrates coeluted during all chromatographic steps. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis showed that the protein was purified to near homogeneity and had a subunit M(r) of 43 000, which is identical with the M(r) of acylase I from porcine kidney and bovine liver. n-Butylmalonic acid was a slow-binding inhibitor of acylase I and inhibited the deacetylation of NAC with a K(i) of 192 ± 27 μM. These results show that acylase I catalyzes the deacetylation of NAC. The acylase I-catalyzed deacetylation of a range of S-alkyl-N- acetyl-L-cysteines, their carbon and oxygen analogues, and the selenium analogue of NAM was also studied with porcine kidney acylase I. The specific activity of the acylase I-catalyzed deacetylation of these substrates was related to their calculated molar volumes and log P values. The S-alkyl-N- acetyl-L-cysteines with short (C0-C3) and unbranched S-alkyl substituents were good acylase I substrates, whereas the S-alkyl-N-acetyl-L-cysteines with long (>C3) and branched S-alkyl substituents were poor acylase I substrates. The carbon and oxygen analogues of S-methyl-N-acetyl-L-cysteine and the carbon analogue of S-ethyl-N-acetyl-L-cysteine were poor acylase I substrates, whereas the selenium analogue of NAM was a good acylase I substrate.
- Uttamsing, Vinita,Keller,Anders
-
p. 800 - 809
(2007/10/03)
-
- METHIONINE SULFONE AND S-SUBSTITUTED CYSTEINE SULFONE DERIVATIVES AS ENZYME INHIBITORS
-
This invention relates to compounds which inhibit thrombin or factor Xa. The compounds contain an aldehyde functionality and a methionine sulfone or S-substituted cysteine sulfone residue. The compounds and their pharmaceutical compositions are useful for preventing thrombosis in mammals which are suspected of having a condition characterized by abnormal thrombosis.
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-
-
- METHIONINE SULFONE AND S-SUBSTITUTED CYSTEINE SULFONE DERIVATIVES AS ENZYME INHIBITORS
-
This invention relates to compounds which inhibit thrombin or factor Xa. The compounds contain an aldehyde functionality and a methionine sulfone or S-substituted cysteine sulfone residue. The compounds and their pharmaceutical compositions are useful for preventing thrombosis in mammals which are suspected of having a condition characterized by abnormal thrombosis.
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-
-
- Methionine sulfone and S-substituted cysteine sulfone derivatives as enzyme inhibitors
-
This invention relates to compounds which inhibit thrombin or factor Xa. The compounds contain an aldehyde functionality and a methionine sulfone or S-substituted cysteine sulfone residue. The compounds and their pharmaceutical compositions are useful for preventing thrombosis in mammals which are suspected of having a condition characterized by abnormal thrombosis.
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-
- L-Methionine related 1-amino acids by acylase cleavage of their corresponding N-acetyl-DL-derivatives
-
Acylase I from Aspergillus oryzae is an even more useful enzyme than suggested so far. Besides standard amino acids such as L-Met, L-Val and L-Phe, a number of additional sulfur- and selenium-containing amino acids can be obtained at useful reaction rates and in very high enantiomeric purity by kinetic resolution of the respective N-acetyl-DL-amino acids.
- Bommarius, Andreas S.,Drauz, Karlheinz,Guenther, Kurt,Knaup, Guenter,Schwarm, Michael
-
p. 3197 - 3200
(2007/10/03)
-
- Amino Acids, 12. - Syntheses of DL-Cysteines from Acrylic Acid Derivatives
-
The addition of sulfenyl chlorides 1 to 2-alkenoic acid esters 2 gives mixtures of 2(3)-chloro-3(2)-thioalkenoic acid esters 3/4, whereas the addition of thiols 7 to methyl 2-chloro-2-propenoate (6) results in the formation of methyl 2-chloro-3-thiopropanoates 3 only.The dependence of the isomerization of 3 to 4 on the reaction conditions was investigated; at higher temperatures the formation of 4 is especially favored.At temperatures below 55 deg C the 2-azido compounds 8 are obtained without isomerization from 3 by reaction with sodium azide in the presence of a PT catalyst.Cysteine derivatives 9 or 10, resp., are obtained by hydrogenation of 8 with H2S/pyridine/H2O or with H2/Re2S; the overall yields of 9 or 10, resp., starting from 6 are as high as 70percent.DL-Cysteine is obtained in good overall yields as hydrochloride hydrate 16 by HCl-catalyzed hydrolysis of the 2-thiazolines 15a*HCl and 15e, which are prepared by HCl-catalyzed addition of thioacetamide (11a) to α-chloroacrylic acid (12) or the amide 13 and consecutive ring closure.
- Effenberger, Franz,Beisswenger, Thomas,Dannenhauer, Fritz
-
p. 2209 - 2224
(2007/10/02)
-
- PURIFICATION AND PROPERTIES OF β-CYANO-L-ALANINE SYNTHASE FROM SPINACIA OLERACEA
-
β-Cyano-L-alanine synthase was purified ca 6200-fold to homogeneity from the leaves of spinach (Spinacia oleracea).The purified enzyme has an apparent Mr of 60 000 and can be dissociated into identical subunits of Mr 30 000.The subunits each contain one molecule of pyridoxal 5'-phosphate.The Km value is 2.3 mM for L-cysteine and 0.73 mM for cyanide. β-Cyano-L-alanine synthase from S. oleracea also catalyses the formation of some S-substituted L-cysteines and some heterocyclic β-substituted alanines from L-cysteine or O-acetyl-L-serine.The specificity of these additional catalytic activities of the purified enzyme are compared with those of cysteine synthase purified from the same plant, and with those of β-cyano-L-alanine synthase purified from other sources.Some other properties, including the amino acid composition of the purified enzyme, are also described. - Key Word Index: Spinacia oleracea; Chenopodiaceae; spinach; β-cyano-L-alanine synthase; cysteine synthase; enzyme purification; amino acid composition; L-cysteine; O-acetyl-L-serine; β-cyano-L-alanine; heterocyclic β-substituted alanines.
- Ikegami, Fumio,Takayama, Kyoko,Tajima, Chiho,Murakoshi, Isamu
-
p. 2011 - 2016
(2007/10/02)
-
- ENZYMATIC SYNTHESIS OF THE NEUROEXCITATORY AMINO ACID QUISQUALIC ACID BY CYSTEINE SYNTHASE
-
Key Word Index - Quisqualis indica var. villosa; Combretaceae; cysteine synthase; isoenzyme; enzyme purification; biosynthesis; heterocyclic β-substituted alanines; quisqualic acid; O-acetyl-L-serine; cysteine.Purification of cysteine synthase from the leaves of Quisqualis indica var. villosa reveals the presence of two forms of this enzyme, separated by chromatography on DEAE-Sephadex A-50.Isoenzyme A was purified 10 000-fold and had a specific activity of 10.8 U/mg protein.Isoenzyme B was purified 460-fold with a specific activity of 0.49 U/mg protein.Both isoenzymes have the same Mrs (58 000) and dissociate into identical subunits (Mr 29 000).The Km value of isoenzyme A is 1.9 mM for O-acetyl-L-serine and 59 μM for sulphide, while that of isoenzyme B is 7.1 mM for O-acetyl-L-serine and 4.0 mM for 3,5-dioxo-1,2,4-oxadiazolidine.Both isoenzymes catalyse the formation of cysteine from O-acetyl-L-serine and hydrogen sulphide, but only isoenzyme B catalyses the formation of L-quisqualic acid.Other significant differences occur in the substrate specificity of the two isoenzymes.Some properties of the purified cysteine synthase isoenzymes are also described.
- Murakoshi, Isamu,Kaneko, Masakazu,Koide, Chiharu,Ikegami, Fumio
-
p. 2759 - 2764
(2007/10/02)
-
- S-substituted 2-azido-3-mercapto-propionic acid ester and process for its production and use
-
The subject matter of the invention are S-substituted 2-azido-3-mercapto-propionic acid esters of the general formula STR1 in which R1 is a methyl or ethyl group and R2 is an unsubstituted or substituted alkyl group, a cycloalkyl group, an unsubstituted or substituted aromatic or heteroaromatic group or a benzyl group, and a process for their production by reaction of a methyl or ethyl ester of 2-chloroacrylic acid with a corresponding thiol to form an S-substituted 2-chloro-3-mercapto-propionic acid ester and subsequently exchanging the chlorine atom with an azido group as well as use of the compounds of formula (I) as intermediate products in the production of D,L-cysteine or derivatives of D,L-cysteine.
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-
- Cysteine derivatives
-
This invention relates to S-alkylcysteines and processes for preparing same. The compounds according to this invention are expected to be applicable as therapeutic agents for hepatic failures.
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-
-
- Micellar Methylating Agents: (Long-chain-alkyl)dimethylsulphonium Iodides
-
Dodecyl-, hexadecyl-, and octadecyl-dimethylsulphonium iodide were found to methylate efficiently various nucleosides, hydroxy aromatic compounds, and thiols at pH 8-11 and 50 - 70 deg C.The optimum conditions and the mechanism of the reaction are discussed briefly in relation to the micellar reaction characteristics.
- Yamauchi, Kiyoshi,Hisanaga, Yorisato,Kinoshita, Masayoshi
-
p. 1941 - 1942
(2007/10/02)
-
- Synthesis of L-Cysteine and Its Analogues by Intact Cells Containing Cysteine Desulfhydrase
-
Cysteine desulfhydrase catalyzes β-replacement, the reverse reaction of α,β-elimination, as well as α,β-elimination.These reactions were studied with intact cells of Aerobacter aerogenes I-3-2 and Aerobacter cloacae IFO 12009 containing cysteine desulfhydrase.L-Cysteine and its analogues were synthesized by replacement and reverse reactions using intact cells. β-Chloro-L-alanine, L-cysteine, S-methyl-L-cysteine, S-allyl-L-cysteine and L-serine were used as substrates together with hydrogen sulfide and methyl mercaptan to synthesize L-cysteine and S-methyl-L-cysteine via replacement reaction by intact cells.L-Cysteine synthesized from β-chloro-L-alanine was confirmed to be entirely in L-form after isolation and identification of the product.The reverse reaction for synthesis of L-cysteine and S-methyl-L-cysteine from hydrogen sulfide or methyl mercaptan, pyruvate and ammonia was also catalyzed by intact cells. β-Chloro-L-alanine was found to be the best substrate for synthesis of L-cysteine and S-methyl-L-cysteine by β-replacement reaction.
- Ohkishi, Haruyuki,Nishikawa, Daikichiro,Kumagai, Hidehiko,Yamada, Hideaki
-
p. 259 - 264
(2007/10/02)
-
- Sulfur containing trialkoxybenzoylamino carboxylic acids
-
Compounds are prepared of the formula: STR1 wherein A is a straight or branched chain alkylene or alkylidene radical having 2 to 5 carbon atoms and which is substituted by an alkylthio group having 1 to 4 carbon atoms, a carboxymethyl thio group, a carboxyethyl thio group, an alkylsulfonyl group having 1 to 4 carbon atoms, a mercapto group, or the substituent on A together with --COR4 forms a 4 to 7 membered thiolactone ring, or A is substituted by an acylmercapto group wherein the acyl is benzoyl, a benzoyl radical substituted with one, two or three alkoxy groups with 1 to 6 carbon atoms, an alkanoyl radical of 1 to 6 carbon atoms, an alkenoyl radical of 3 to 6 carbon atoms, R1, R2 and R3 are the same or different and are alkyl groups of 1 to 5 carbon atoms and one of R1, R2 and R3 also can be hydrogen or the acyl radical of an alkanoic acid of 2 to 4 carbon atoms and R4 is a hydroxy group or an alkoxy group with 1 to 5 carbon atoms and their pharmacologically acceptable salts. The compounds are pharmacodynamically active and are suited for prophylaxis and treatment of heart illnesses such as cardiac ischemia, cardiac infarct, heart rhythm and circulatory disturbances.
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-
- Pyrimidinylpropenamides as antitumor agents. Analogues of the antibiotic sparsomycin
-
A series of pyrimidinylpropenamides 9 and their oxidation products 10 was prepared, as analogues of sparsomycin (1), for antitumor evaluation. Syntheses involved condensation of the appropriate amino alcohol 5 with acid 8. The resulting sulfides 9 were then oxidized with NaIO4 or H2O2 to sulfoxides 10. Activity was studied in lymphocytic leukemia P-388 and KB cell culture. With the exception of the n-decyl analogue, all of the deoxygenated compounds 9 were inactive regardless of the sterochemical form. In the sulfoxide series 10, those compounds prepared with an L configuration at the asymmetric carbon were also inactive. The completely racemic sulfoxides, on the other hand, displayed substantial antitumor activity (ILS=37-61% in P-388; ED50=1.2-2.4μg/ml in KB) suggesting that both the presence of a sulfoxide moiety and a D configuration at the chiral carbon atom were structural requirements for a positive antitumor response. There appeared to be a large tolerance for the group substituted at the sulfoxide moiety, however.
- Lin,Dubois
-
p. 337 - 341
(2007/10/06)
-