- Biosynthesis of the antibiotic tropodithietic acid by the marine bacterium Phaeobacter inhibens
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The biosynthesis of tropodithietic acid was investigated using a combinatorial approach of feeding experiments, gene knockouts and bioinformatic analyses. The mechanism of sulfur introduction is distinct from known mechanisms in holomycin, thiomarinol A a
- Brock, Nelson L.,Nikolay, Alexander,Dickschat, Jeroen S.
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Read Online
- Thioamycolamides A-E, Sulfur-Containing Cycliclipopeptides Produced by the Rare Actinomycete Amycolatopsis sp.
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A series of novel sulfur-containing cycliclipopeptides named thioamycolamides A-E, with thiazoline, thioether rings, and fatty acid moieties, were identified from the culture broth of the rare actinomycete Amycolatopsis sp. 26-4. The planar structural elu
- Pan, Chengqian,Kuranaga, Takefumi,Liu, Chao,Lu, Shan,Shinzato, Naoya,Kakeya, Hideaki
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Read Online
- Synthesis and Biological Evaluation of CF3Se-Substituted α-Amino Acid Derivatives
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Several CF3Se-substituted α-amino acid derivatives, such as (R)-2-amino-3-((trifluoromethyl)selanyl)propanoates (5 a/6 a), (S)-2-amino-4-((trifluoromethyl)selanyl)butanoates (5 b/6 b), (2R,3R)-2-amino-3-((trifluoromethyl)selanyl)butanoates (5 c/6 c), (R)-2-((S)-2-amino-3-phenylpropanamido)-3-((trifluoromethyl)selanyl)propanoates (11 a/12 a), and (R)-2-(2-aminoacetamido)-3-((trifluoromethyl)selanyl)propanoates (11 b/12 b), were readily synthesized from natural amino acids and [Me4N][SeCF3]. The primary in vitro cytotoxicity assays revealed that compounds 6 a, 11 a and 12 a were more effective cell growth inhibitors than the other tested CF3Se-substituted derivatives towards MCF-7, HCT116, and SK-OV-3 cells, with their IC50 values being less than 10 μM for MCF-7 and HCT116 cells. This study indicated the potentials of CF3Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.
- Han, Zhou-Zhou,Dong, Tao,Ming, Xiao-Xia,Kuang, Fu,Zhang, Cheng-Pan
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p. 3177 - 3180
(2021/07/28)
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- Synthesis, Fungicidal Activity, and Mechanism of Action of Pyrazole Amide and Ester Derivatives Based on Natural Products l -Serine and Waltherione Alkaloids
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The development of new green fungicides based on the structural optimization of natural products can effectively solve the problems of low safety and high pathogen resistance of traditional fungicides. In this paper, based on pyrazole amide compound h-I-9 with excellent fungicidal activity discovered in the previous work, a series of l-serine-derived pyrazole amide and waltherione alkaloid-derived pyrazole ester derivatives were synthesized. The structures were successively identified by 1H NMR, 13C NMR, high-resolution mass spectrometry, and X-ray single-crystal diffraction. The in vitro and in vivo fungicidal activity screening demonstrated that compound II-5 showed a good inhibition rate against Physalospora piricola. A transmission electron microscope and fluorescence microscope observation further revealed that compound II-5 may cause damage to the cell membranes and vacuoles, and the hyphae treated with II-5 could produce obvious and easily observed blue fluorescence. The succinate dehydrogenase (SDH) enzymatic activity and molecular docking simulation indicated that compounds I-3 and I-4 may be potential SDH inhibitors against Alternaria sp.
- Chen, Yan,Cui, Yanhong,Gu, Yucheng,Guo, Shangjing,Hua, Xuewen,Liu, Wenrui,Liu, Xinghai,Liu, Yi,Ru, Jing,Sui, Junkang,Wang, Guiqing,Xue, Chenmeng,Yu, Xiaobo
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p. 11470 - 11484
(2021/10/12)
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- FUSED HETEROCYCLIC BENZODIAZEPINE DERIVATIVES AND USES THEREOF
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The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.
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Page/Page column 130
(2020/05/29)
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- SYNTHESIS OF 4-CHLOROKYNURENINES AND INTERMEDIATES
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The invention relates to an overall enantio-specific synthesis of 4-chlorokynurenine compounds, in particular L-4-chlorokynurenine, with improved yields. Large-scale syntheses are disclosed. The invention also relates to novel intermediates in the synthes
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Paragraph 48-69
(2019/08/29)
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- NOVEL BENZODIAZEPINE DERIVATIVES AND USES THEREOF
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The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.
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Paragraph 0597-0599
(2019/12/24)
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- Enantioselective Anion Recognition by Chiral Halogen-Bonding [2]Rotaxanes
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The application of chiral interlocked host molecules for discrimination of guest enantiomers has been largely overlooked, which is surprising given their unique three-dimensional binding cavities capable of guest encapsulation. Herein, we combined the stringent linear geometric interaction constraints of halogen bonding (XB), the noncovalent interaction between an electrophilic halogen atom and a Lewis base, with highly preorganized and conformationally restricted chiral cavities of [2]rotaxanes to achieve enantioselective anion recognition. Representing the first detailed investigation of the use of chiral XB rotaxanes for this purpose, extensive 1H NMR binding studies and molecular dynamics (MD) simulation experiments revealed that the chiral rotaxane cavity significantly enhances enantiodiscrimination compared to the non-interlocked free axle and macrocycle components. Furthermore, by examining the enantioselectivities of a family of structurally similar XB [2]rotaxanes containing different combinations of chiral and achiral macrocycle and axle components, the dominant influence of the chiral macrocycle in our rotaxane design for determining the effectiveness of chiral discrimination is demonstrated. MD simulations reveal the crucial geometric roles played by the XB interactions in orientating the bound enantiomeric anion guests for chiral selectivity, as well as the critical importance of the anions' hydration shells in governing binding affinity and enantiodiscrimination.
- Lim, Jason Y. C.,Marques, Igor,Félix, Vítor,Beer, Paul D.
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supporting information
p. 12228 - 12239
(2017/09/12)
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- Improved synthetic routes to the selenocysteine derivatives useful for Boc-based peptide synthesis with benzylic protection on the selenium atom
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Selenocysteine (Sec) derivatives, i.e., Boc-Sec(MBn)-OH (1) and Boc-Sec(MPM)-OH (2), which are useful for chemical synthesis of selenopeptides, were obtained from L-serine in five steps with total yields of 73% and 74%, respectively. The enantiomeric excesses were confirmed to be >99% e.e. by optical resolution using a chiral column on HPLC. On the other hand, for the case of a Fmoc-protected Sec derivative, i.e., Fmoc-Sec(MPM)-OH, similar reactions resulted in low yields and partial racemization taking place. [PRESENTED EQUATION]
- Shimodaira, Shingo,Iwaoka, Michio
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p. 260 - 271
(2017/03/09)
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- Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid
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The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.
- Boibessot, Thibaut,Bénimèlis, David,Jean, Marion,Benfodda, Zohra,Meffre, Patrick
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supporting information
p. 2685 - 2688
(2016/11/30)
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- HETEROCYCLIC DERIVED METALLOPROTEASE INHIBITORS
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This invention provides novel heterocyclic derived matrix metalloprotease inhibitors of the formula: and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by antagonizing matrix metalloproteases. This invention also provides therapeutic and prophylactic methods using the instant pharmaceutical compositions.
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Page/Page column 57
(2008/06/13)
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- Syntheses and in vitro evaluation of arylsulfone-based MMP inhibitors with heterocycle-derived zinc-binding groups (ZBGs)
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Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6- to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. Although a number of 6- and 7-membered hetero
- Zhang, Yue-Mei,Fan, Xiaodong,Yang, Shyh-Ming,Scannevin, Robert H.,Burke, Sharon L.,Rhodes, Kenneth J.,Jackson, Paul F.
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p. 405 - 408
(2008/12/23)
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- Synthetic seleno-glutaredoxin 3 analogues are highly reducing oxidoreductases with enhanced catalytic efficiency
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Selenoenzymes have a central role in maintaining cellular redox potential. These enzymes have selenenylsulfide bonds in their active sites that catalyze the reduction of peroxides, sulfoxides, and disulfides. The selenol/disufide exchange reaction is comm
- Metanis, Norman,Keinan, Ehud,Dawson, Philip E.
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p. 16684 - 16691
(2007/10/03)
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- Internally stabilized selenocysteine derivatives: Syntheses, 77Se NMR and biomimetic studies
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Selenocystine ([Sec]2) and aryl-substituted selenocysteine (Sec) derivatives are synthesized, starting from commercially available amino acid L-serine. These compounds are characterized by a number of analytical techniques such as NMR (1H, 13C and 77Se) and TOF mass spectroscopy. This study reveals that the introduction of amino/imino substituents capable of interacting with selenium may stabilize the Sec derivatives. This study further suggests that the oxidation-elimination reactions in Sec derivatives could be used for the generation of biologically active selenols having internally stabilizing substituents. The Royal Society of Chemistry 2005.
- Phadnis, Prasad P.,Mugesh
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p. 2476 - 2481
(2007/10/03)
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- Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues
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Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.
- Bhat, Ramakrishna G.,Porhiel, Emmanuel,Saravanan, Vadivelu,Chandrasekaran, Srinivasan
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p. 5251 - 5253
(2007/10/03)
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- Synthesis of a selenocysteine-containing peptide by native chemical ligation
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(equation presented) A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.
- Gieselman, Matt D.,Xie, Lili,Van Der Donk, Wilfred A.
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p. 1331 - 1334
(2007/10/03)
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- Synthesis of Se- and Te-Containing Amino Acids: Useful Probes for Structural Studies of Proteins.
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The synthesis of (1)-Se-cystine, (1)-[77Se]-cystine and (1)-Te-cystine in 4 steps from commercially available 2(S)-[(tert-butoxycarbonyl)amino]-3-hydroxy-propionate has been accomplished. [4-13C]Te-Met has been synthesized in a one pot reaction.
- Silks, L. A. "Pete"
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p. 611 - 616
(2007/10/03)
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- Synthesis of L-selenocystine, L-[77Se]selenocystine and L-tellurocystine
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Synthetic routes for the synthesis of stable isotope labelled amino acids which contain either a selenium or a tellurium atom have been explored. L-Selenocystine, L-[77Se]selenocystine and L-tellurocystine have been constructed in four steps from commercially available methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionate. The sequence of reactions has been successfully scaled up giving significant quantities of the chalcogen based amino acids in fair to good overall yield. Copyright 1997 by the Royal Society of Chemistry.
- Stocking, Emily M.,Schwarz, Jessie N.,Senn, Hans,Salzmann, Michael,Silks, Louis A.
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p. 2443 - 2447
(2007/10/03)
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- Enantioselective synthesis of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine; agents suitable for the solid-phase synthesis of peptides containing nonhydrolyzable analogues of O-phosphotyrosine
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Enantioselective convergent syntheses of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine are reported.
- Smyth,Burke Jr.
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p. 551 - 554
(2007/10/02)
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- Intramolecular Pictet-Spengler Reaction of N-Alkoxytryptamines. 3. Stereoselective Synthesis of (-)-Debromoeudistomin L and (-)-O-Methyldebromoeudistomin E and Their Stereoisomers
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The N-hydroxytrypamines 10 and 11 were converted into the N-alkoxy derivatives 32-34 (overall yield 57-72percent) by successive protection with chloroformate providing 27 and 28, reaction with functionalized chloromethyl sulfides, and deprotection with a "naked" fluoride.Intramolecular cyclization succeeded with 33 and 34 by reduction of the methyl ester with DIBAL and treatment with TFA to give diastereomeric pairs with a slight selectivity for the trans isomer (53-81percent, cis/trans ca. 35/65).Removal of the BOC group gave debromoeudistomin L ((-)-1e), its three stereoisomers (42a,b and (+)-1e), O-methyldebromoeudistomin E ((-)-1f), and its stereomer 43.
- Hermkens, Pedro H. H.,Maarseveen, Jan H. v.,Ottenheijm, Harry C. J.,Kruse, Chris G.,Scheeren, Hans W.
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p. 3998 - 4006
(2007/10/02)
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- 1,2,4-trisubstituted diazolidinones
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1,2,4-Trisubstituted diazolidinones are intermediates to bicyclic pyrazolidinone antimicrobial compounds.
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- A NOVEL APPROACH TO THE SYNTHESIS OF OPTICALLY PURE NON PROTEIN α-AMINO ACIDS IN BOTH L AND D CONFIGURATIONS FROM L-SERINE
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Efficient syntheses of (2R)-2-Boc-amino-3-phenylsulfonyl-1-propanol 3 and its enantiomer 9 from L-serine are described.The potential of these compounds in a novel general method for the synthesis of optically pure non protein α-amino acids in both the L and D configurations is exemplified by the preparation of N-Boc-L-and D-homophenylalanine,-norvaline and -norleucine.
- Sasaki, N.Andre,Hashimoto, Chiyomi,Potier, Pierre
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p. 6069 - 6072
(2007/10/02)
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- LES ORGANOCUPRATES DANS UNE NOUVELLE SYNTHESE D'AMINOACIDES ENANTIOMERIQUEMENT PURS
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A new general method of synthesis of optically pure α- amino esters was elaborated during studies on the reaction of organocuprates with tosyl and halogeno derivatives of L-serine and L-homoserine.
- Bajgrowicz, J. A.,Hallaoui, A. El,Jacquier, R.,Pigiere, Ch.,Viallefont, Ph.
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p. 1833 - 1845
(2007/10/02)
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