23508-35-2Relevant articles and documents
Aeruginosins 102-A and B, new thrombin inhibitors from the cyanobacterium Microcystis viridis (NIES-102)
Matsuda, Hisashi,Okino, Tatsufumi,Murakami, Masahiro,Yamaguchi, Katsumi
, p. 14501 - 14506 (1996)
Aeruginosins 102-A and B were isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-102). Their structures were elucidated to be 1 and 2 on the basis of 2D NMR data and chemical degradation. These peptides inhibited thrombin potently.
A Phenylpyruvic Acid Reductase Is Required for Biosynthesis of Tropane Alkaloids
Qiu, Fei,Yang, Chunxian,Yuan, Lina,Xiang, Dan,Lan, Xiaozhong,Chen, Min,Liao, Zhihua
, p. 7807 - 7810 (2018)
Solanaceous medicinal plants produce tropane alkaloids (TAs). We discovered a novel gene from Atropa belladonna, AbPPAR, which encodes a phenylpyruvic acid reductase required for TA biosynthesis. AbPPAR was specifically expressed in root pericycles and endodermis. AbPPAR was shown to catalyze reduction of phenylpyruvic acid to phenyllactic acid, a precursor of TAs. Suppression of AbPPAR disrupted TA biosynthesis through reduction of phenyllactic acid levels. In summary, we identified a novel enzyme involved in TA biosynthesis.
Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
Shimada, Naoyuki,Takahashi, Naoya,Ohse, Naoki,Koshizuka, Masayoshi,Makino, Kazuishi
supporting information, p. 13145 - 13148 (2020/11/09)
The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B and C.
Mechanistic study of the radical SAM-dependent amine dehydrogenation reactions
Ji, Xinjian,Liu, Wan-Qiu,Yuan, Shuguang,Yin, Yue,Ding, Wei,Zhang, Qi
, p. 10555 - 10558 (2016/09/02)
The radical SAM enzyme NosL catalyzes the conversion of l-Trp to 3-methyl-2-indolic acid, and this reaction is initiated by the 5′-deoxyadenosyl (dAdo) radical-mediated hydrogen abstraction from the l-Trp amino group. We demonstrate here that when d-Trp was used in the NosL reaction, hydrogen abstraction occurs promiscuously at both the amino group and Cα of d-Trp. These results inspired us to establish the detailed mechanism of l-Trp amine dehydrogenation catalyzed by a NosL mutant, and to engineer a novel radical SAM-dependent l-Tyr amine dehydrogenase from the thiamine biosynthesis enzyme ThiH.
Latifolicinin A from a Fermented Soymilk Product and the Structure-Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth
Ke, Yi-Yu,Tsai, Chen-Hsuan,Yu, Hui-Ming,Jao, Yu-Chen,Fang, Jim-Min,Wong, Chi-Huey
, p. 9715 - 9721 (2015/11/24)
The functional components in soymilk may vary depending upon the fermentation process. A fermented soymilk product (FSP) obtained by incubation with the microorganisms of intestinal microflora was found to reduce the risk of breast cancer. Guided by the inhibitory activities against breast cancer cells, two cytotoxic compounds, daidzein and (S)-latifolicinin A, were isolated from the FSP by repetitive extraction and chromatography. Latifolicinin A is the n-butyl ester of β-(4-hydroxyphenyl)lactic acid (HPLA). A series of the ester and amide derivatives of (S)-HPLA and l-tyrosine were synthesized for evaluation of their cytotoxic activities. In comparison, (S)-HPLA derivatives exhibited equal or superior inhibitory activities to their l-tyrosine counterparts, and (S)-HPLA amides showed better cytotoxic activities than their corresponding esters. In particular, (S)-HPLA farnesyl amide was active to triple-negative MDA-MB-231 breast cancer cells (IC50 = 27 μM) and 10-fold less toxic to Detroit-551 normal cells.
Biocontrolled formal inversion or retention of L -α-amino acids to enantiopure (R)- or (S)-hydroxyacids
Busto, Eduardo,Grischek, Barbara,Kroutil, Wolfgang,Richter, Nina
supporting information, p. 11225 - 11228,4 (2015/01/07)
Natural L-α-amino acids and L-norleucine were transformed to the corresponding α-hydroxy acids by formal biocatalytic inversion or retention of absolute configuration. The one-pot transformation was achieved by a concurrent oxidation reduction cascade in aqueous media. A representative panel of enantiopure (R)- and (S)-2-hydroxy acids possessing aliphatic, aromatic and heteroaromatic moieties were isolated in high yield (67-85 %) and enantiopure form (>99 % ee) without requiring chromatographic purification.
Concise, protecting group free total syntheses of (+)-sattabacin and (+)-4-hydroxysattabacin
Aronoff, Matthew R.,Bourjaily, Neil A.,Miller, Kenneth A.
scheme or table, p. 6375 - 6377 (2011/01/03)
The first asymmetric total syntheses of the antiviral natural products (+)-sattabacin and (+)-4-hydroxysattabacin are reported. Both total syntheses are remarkably concise and were completed without the use of protecting groups. These syntheses allowed the unambiguous assignment of the absolute configuration of both natural products. The syntheses of these natural products, which exhibit marked antiviral activity, are readily amenable to the preparation of structural analogs and progress in this regard is also reported.
4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARα/γ agonists. Part I: Synthesis and pharmacological evaluation
Parmenon, Cecile,Guillard, Jerome,Caignard, Daniel-Henri,Hennuyer, Nathalie,Staels, Bart,Audinot-Bouchez, Valerie,Boutin, Jean-Albert,Dacquet, Catherine,Ktorza, Alain,Viaud-Massuard, Marie-Claude
, p. 1617 - 1622 (2008/09/19)
Type-2 diabetes (T2D) is a complex metabolic disease characterized by insulin resistance in the liver and peripheral tissues accompanied by a defect in pancreatic β-cell. Since their discovery three subtypes of Peroxisomes Proliferators Activated Receptors were identified namely PPARα, PPARγ and PPARβ/(δ). We were interested in designing novel PPARγ selective agonists and/or dual PPARα/γ agonists. Based on the typical topology of synthetic PPAR agonists, we focused our design approach on 4,4-dimethyl-1,2,3,4-tetrahydroquinoline as novel cyclic tail.
METHOD FOR SYNTHESIS OF KETO ACID OR AMINO ACID BY HYDRATION OF ACETHYLENE COMPOUND
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Page/Page column 24, (2008/12/06)
An object of the present invention is to provide a method for synthesis of keto acids by hydration of an acetylene compound (acetylene-carboxylic acids) under mild conditions free from harmful mercury catalysts and a method for synthesis of amino acids from acetylene-carboxylic acids in a single container (one-pot or tandem synthesis). In one embodiment of the method according to the present invention for synthesis of keto acids, acetylene-carboxylic acids is hydrated in the presence of a metal salt represented by General Formula (1), where M1 represents an element in Group VIII, IX, or X of the periodic table, and X1, X2, or X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k × m = L × n.
An asymmetric synthesis of PPAR-γ agonist navaglitazar from (+)-methyl (2S,3R)-3-(4-methoxyphenyl)glycidate
Rizzo, John R.,Zhang, Tony Y.
, p. 580 - 583 (2007/10/03)
An asymmetric synthesis of navaglitazar, a peroxisome proliferator activated receptor (PPAR) γ agonist, from commercially available (+)-methyl (2S,3R)-3-(4-methoxyphenyl)glycidate, is described. The new synthesis features high overall yield, low solvent usage, crystalline intermediates and operational simplicity. Schweizerische Chemische Gesellschaft.
