- Evaluation of a cell penetrating prenylated peptide lacking an intrinsic fluorophore via in situ click reaction
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Protein prenylation involves the addition of either a farnesyl (C 15) or geranylgeranyl (C20) isoprenoid moiety onto the C-terminus of many proteins. This natural modification serves to direct a protein to the plasma membrane of the
- Ochocki, Joshua D.,Mullen, Daniel G.,Wattenberg, Elizabeth V.,Distefano, Mark D.
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- Identification and optimization of quinolone-based inhibitors against cytochrome bd oxidase using an electrochemical assay
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A target-focused library of small molecules, containing a set of quinones, quinolones, coumarins, flavonoids and other diverse drugs was screened to identify potential inhibitors of the cytochrome bd-I oxidase from Escherichia coli by means of an electroc
- Makarchuk,Nikolaev,Thesseling,Dejon,Lamberty,Stief,Speicher,Friedrich,Hellwig,Nasiri,Melin
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- Total synthesis of geranylgeranylglyceryl phosphate enantiomers: Substrates for characterization of 2,3-O-digeranylgeranylglyceryl phosphate synthase
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To determine the enantioselectivity of (S)-2,3-di-O-geranylgeranylglyceryl phosphate synthase (DGGGPS) from the thermoacidophilic archaeon Sulfolobus solfataricus, we developed an efficient enantioselective route to the enantiomeric geranylgeranylglyceryl phosphates (R)-GGGP and (S)-GGGP. Previous routes to these substrates involved enzymatic conversions due to the lability of the polyprenyl chains toward common phosphorylation reaction conditions. The synthesis described herein employs a mild trimethyl phosphite/carbon tetrabromide oxidative phosphorylation to circumvent this problem. In contrast to previous results suggesting that only (S)-GGGP can act as the prenyl acceptor substrate, both (R)-GGGP and (S)-GGGP were found to be substrates for DGGGPS.
- Zhang, Honglu,Shibuya, Kyohei,Hemmi, Hisashi,Nishino, Tokuzo,Prestwich, Glenn D.
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- Substrate specificities of several prenyl chain elongating enzymes with respect to 4-methyl-4-pentenyl diphosphate
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In order to develop synthetic methods for biologically active homoallylic terpene sulfates, we examined the applicability and substrate specificities of several prenyl chain elongating enzymes with respect to 4-methyl-4-pentenyl diphosphate (homoIPP). The reaction of dimethylallyl diphosphate with homoIPP by use of Bacillus stearothermophilus (all-trans)-farnesyl diphosphate synthase resulted in efficient yields of cis-(yield: 45.9%) and trans-4,8-dimethylnona-3, 7-dien-1-ol (homoGOH, 25.5%), which has a carbon skeleton of 4,8-dimethylnona-3-en-1-sulfate, an antiproliferative compound from a marine organism (Aiello, A. et al., Tetrahedron, 53, 11489-11492 (1997)). The homoIPP was found to be also active as a homoallylic substrate in place of isopentenyl diphosphate for Sulfolobus acidocaldarius geranylgeranyl diphosphate synthase to give diphosphate of cis- and trans-4,8,12-trimethyltrideca-3,7,11-trien-1-ol, for Micrococcus luteus B-P 26 hexaprenyl diphosphate synthase to give cis- and trans-4,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-ol (homoGGOH), and for Micrococcus luteus B-P 26 undecaprenyl diphosphate synthase to give cis-homoGGOH exclusively.
- Nagaki, Masahiko,Miki, Yohei,Nakada, Minori,Kawakami, Jun,Kitahara, Haruo,Maki, Yuji,Gotoh, Yoshinori,Nishino, Tokuzo,Koyama, Tanetoshi
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- S-Geranylgeranyl-l-glutathione is a ligand for human B cell-confinement receptor P2RY8
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Germinal centres are important sites for antibody diversification and affinity maturation, and are also a common origin of B cell malignancies. Despite being made up of motile cells, germinal centres are tightly confined within B cell follicles. The cues that promote this confinement are incompletely understood. P2RY8 is a Gα13-coupled receptor that mediates the inhibition of migration and regulates the growth of B cells in lymphoid tissues1,2. P2RY8 is frequently mutated in germinal-centre B cell-like diffuse large B cell lymphoma (GCB-DLBCL) and Burkitt lymphoma1,3–6, and the ligand for this receptor has not yet been identified. Here we perform a search for P2RY8 ligands and find P2RY8 bioactivity in bile and in culture supernatants of several mouse and human cell lines. Using a seven-step biochemical fractionation procedure and a drop-out mass spectrometry approach, we show that a previously undescribed biomolecule, S-geranylgeranyl-l-glutathione (GGG), is a potent P2RY8 ligand that is detectable in lymphoid tissues at the nanomolar level. GGG inhibited the chemokine-mediated migration of human germinal-centre B cells and T follicular helper cells, and antagonized the induction of phosphorylated AKT in germinal-centre B cells. We also found that the enzyme gamma-glutamyltransferase-5 (GGT5), which was highly expressed by follicular dendritic cells, metabolized GGG to a form that did not activate the receptor. Overexpression of GGT5 disrupted the ability of P2RY8 to promote B cell confinement to germinal centres, which?indicates that GGT5 establishes a GGG gradient in lymphoid tissues. This work defines GGG as an intercellular signalling molecule?that is involved in organizing and controlling germinal-centre responses. As the P2RY8 locus is modified in several other types of?cancer in addition to GCB-DLBCL and Burkitt lymphoma, we speculate that GGG might have organizing and growth-regulatory roles in multiple human tissues.
- Lu, Erick,Wolfreys, Finn D.,Muppidi, Jagan R.,Xu, Ying,Cyster, Jason G.
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- Coumarin derivatives for cancer therapy
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The disclosure provides methods and compositions for treating and preventing cancer using 6-substituted coumarin derivatives. The coumarin derivatives of the disclosure have substituents at the 6-position with five carbon atoms or greater. The coumarin derivatives may be further substituted and may be 3,4-dihydrocoumarins. In preferred embodiments, the coumarin derivatives of the disclosure are used to treat pancreatic cancer.
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Page/Page column 25; 26
(2016/08/17)
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- GGA DERIVATIVES
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This invention relates to geranylgeranyl acetone (GGA) derivatives, pharmaceutical compositions comprising GGA derivatives and the use of GGA derivatives.
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Paragraph 0340; 0343
(2015/05/26)
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- METHODS FOR TREATING NEURON DAMAGE
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This invention relates to the use of geranylgeranyl acetone (GGA), its isomers, and GGA derivatives in a method for for treating a disease in a subject mediated in part by miRNA-378 or miRNA-711 increased activity comprising administering to the subject a therapeutically effective amount of 5-trans-GGA or a derivative thereof.
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Paragraph 0294
(2014/07/22)
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- GGA AND GGA DERIVATIVES COMPOSITIONS THEREOF AND METHODS FOR TREATING NEURODEGENERATIVE DISEASES INCLUDING PARALYSIS INCLUDING THEM
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This invention relates to geranylgeranyl acetone (GGA) derivatives and the use of GGA, its isomers, and GGA derivatives in methods for inhibiting neural death, increasing neural activity, increasing axon growth and cell viability, and increasing the survival rate of subjects administered the GGA or GGA derivatives.
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Paragraph 0282
(2014/10/18)
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- GERANYLGERANYLACETONE DERIVATIVES
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Provided herein are geranylgeranylacetone derivatives and methods of using them.
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Paragraph 0178
(2013/04/13)
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- GGA AND GGA DERIVATIVES, COMPOSITIONS THEREOF AND METHODS FOR TREATING NEURODEGENERATIVE DISEASES INCLUDING PARALYSIS INCLUDING THEM
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This invention relates to geranylgeranyl acetone (GGA) derivatives and the use of GGA, its isomers, and GGA derivatives in methods for inhibiting neural death, increasing neural activity, increasing axon growth and cell viability, and increasing the survival rate of subjects administered the GGA or GGA derivatives.
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Paragraph 0270
(2013/09/12)
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- Synthesis of isoprenoid chain-contained chemical probes for an investigation of molecular interactions by using quartz crystal microbalance
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Five probes including four that contained isoprenoid chain were synthesized. These probes were assembled onto the gold-coated quartz crystal chips for analysis of their interactions with four yeast proteins by using the quartz crystal microbalance technology. Results showed that 3-phosphoglycerate phosphokinase and triosephosphate isomerase had clear interactions with certain probes, while glutathione reductase and phosphoglucose isomerase gave much lower interaction signals. It also suggested that 3-phosphoglycerate phosphokinase had two sites interacting with the probe attached with a geranyl moiety. Further molecule simulation experiments provided supportive information on these intermolecular interactions. Together, our data suggested that there are hydrophobic interactions, with relatively good selectivity, between isoprenoid chain and proteins.
- Liu, Wujun,Zhang, Yixin,Hou, Shuhua,Zhao, Zongbao Kent
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supporting information
p. 6208 - 6210
(2013/10/22)
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- A convergent stereocontrolled synthesis of [3-14C]solanesol
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In this communication, we report the synthesis of 5 mCi of [3- 14C]solanesol (1) prepared from ethyl [3-14C]acetoacetate and (all-E)-octaprenyl bromide (2) in four steps, with a specific radioactivity of 19.83 mCi/mmol and with a chemical/ stereochemical and radiochemical purity of ≥ 95%. (Figure 1). Position 3 of the chain was selected for 14C labelling because of the metabolic stability of this position. Unlabelled (all-E)-octaprenyl (18) (Scheme 4) necessary for this work was prepared via a convergent iterative 'allyl-allyl' coupling approach of precursors easily derived from readily available inexpensive starting materials. Copyright
- Roe, Stephen J.,Oldfield, Mark F.,Geach, Neil,Baxter, Andrew
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p. 485 - 491
(2014/03/21)
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- METHODS FOR TREATING NEURODEGENERATIVE DISEASES
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This invention relates to the 5-cis and 5-trans isomers of geranylgeranyl acetone, preferably such synthetic isomers, and pharmaceutical compositions containing such isomers. Other aspects of this invention relate to the use of geranylgeranyl acetone and its isomers in methods for inhibiting neural death, increasing neural activity, and increasing axon growth and cell viability. Geranylgeranyl acetone is a known anti-ulcer drug used commercially and in clinical situations. GGA has also been shown to exert cytoprotective effects on a variety of organs, such as the eye, brain, and heart.
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(2012/03/26)
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- Stereoselective Friedel-Crafts alkylation catalyzed by squalene hopene cyclases
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In organic synthesis the Friedel-Crafts alkylation is of eminent importance, as it is a key reaction in many synthetic routes. A general access to enzymatic Friedel-Crafts alkylations would be very beneficial due to the high selectivity of biocatalysts. We used designed polyprenyl phenyl ethers to specifically address this reaction by using squalene hopene cyclases as catalysts. Polycyclic products with aromatic rings constituting important biological active compounds were obtained. Our results demonstrate that squalene hopene cyclases can be utilized for Friedel-Crafts alkylations and reveal the potential of these enzymes for chiral Bronsted acid catalysis.
- Hammer, Stephan C.,Dominicus, J?rg M.,Syrén, Per-Olof,Nestl, Bettina M.,Hauer, Bernhard
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experimental part
p. 7624 - 7629
(2012/09/21)
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- Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative
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A series of hydroxycoumarin derivatives has been synthesized and evaluated against human pancreatic PANC-1 cancer cells under nutrient-deprived conditions. Several compounds exhibited 100% preferential cytotoxicity at low micromolar concentrations under n
- Devji, Tehsina,Reddy, Claire,Woo, Christina,Awale, Suresh,Kadota, Shigetoshi,Carrico-Moniz, Dora
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p. 5770 - 5773
(2011/10/18)
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- Carbenium ion trapping using sulfonamides: an acid-catalysed synthesis of pyrrolidines by intramolecular hydroamination
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Cyclisations of homoallylic sulfonamides proceed smoothly via carbenium ion generation using trifluoromethanesulfonic (triflic) acid, the ease of cyclisation being directly related to the ion stability to give good to excellent yields of the corresponding pyrrolidines. Both toluene- and nitrophenyl-sulfonyl groups are suitable for all substrates tested whereas the corresponding carbamates are only useful in cases of tertiary and highly stabilised carbenium ions. Polyene-derived sulfonamides can also be cyclised to the corresponding polycyclic systems in remarkably high yields, in reactions reminiscent of related cascades encountered in terpene biosynthesis.
- Griffiths-Jones (née Haskins), Charlotte M.,Knight, David W.
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experimental part
p. 4150 - 4166
(2010/07/05)
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- Multifunctional prenylated peptides for live cell analysis
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Protein prenylation is a common post-translational modification present in eukaryotic cells. Many key proteins involved in signal transduction pathways are prenylated, and inhibition of prenylation can be useful as atherapeutic intervention. While significant progress has been made in u nderstanding protein prenylation in vitro, we have been interested in studying this process in living cells, including the question of where prenylated molecules localize. Here, we describe the synthesis and live cell analysis of a series of fluorescently labeled multifunctional peptides, based on the C-terminus of the naturally prenylated protein CDC42. A synthetic route was developed that features a key Acm to Scm protecting group conversion. This strategy was compatible with acid-sensitive isoprenoid moieties and allowed incorporation of an appropriate fluorophore aswell as a cell-penetrating sequence (penetratin). These peptides are ab le to enter cells through different mechanisms, depending on the presence or absence of the penetratin vehicle and the nature of the prenyl group attached. Interestingly, prenylated peptides lacking penetratin are able to enter cells freely through an energy-independent process and localize in a perinuclear fashion. This effect extends to a prenylated peptide that includes a full "CAAX box" sequence (specifically, CVLL). Hence, these peptides open the door for studies of protein prenylation in living cells, including enzymatic processing and intracellular peptide trafficking. Moreover, the synthetic strategy developed here should be useful for the assembly of other types of peptides that contain acid-sensitive functionalities.
- Wollack, James W.,Zeliadt, Nicholette A.,Mullen, Daniel G.,Amundson, Gregg,Geier, Suzanne,et al.
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experimental part
p. 7293 - 7303
(2009/10/17)
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- PHENYL-PRENYL DERIVATIVES, OF MARINE AND SYNTHETIC ORIGIN, FOR THE TREATMENT OF COGNITIVE, NEURODEGENERATIVE OR NEURONAL DISEASES OR DISORDERS
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The present invention is related to a family of phenyl-prenyl derivatives of formula (I), and to their use in the treatment of cognitive, neurodegenerative or neuronal diseases or disorders, such as Alzheimer's disease or Parkinson's Disease. The present
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Page/Page column 32
(2009/10/09)
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- Enantioselective total synthesis of (+)-sarcodictyenone
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The first enantioselective total synthesis of (+)-sarcodictyenone is described [4.3% overall yield from (5R,6R)-6-methyl-5-trimethylsily-2-cyclohexenone]. This work establishes the absolute stereochemistry of the natural product.
- Yamazaki, Takako,Ishikawa, Minoru,Uemura, Miki,Kanda, Yuko,Takei, Hisashi,Asaoka, Morio
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p. 1895 - 1900
(2008/09/17)
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- General preparation and controlled cyclization of acyclic terpenoids
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A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C5 unit 5 and the chain-termination process utilizing the C5 unit 10 to
- Kuk, Jinchul,Beom, Soo Kim,Jung, Heejung,Choi, Seyoung,Park, Jung-Youl,Koo, Sangho
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p. 1991 - 1994
(2008/09/18)
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- An improved convergent strategy for the synthesis of oligoprenols
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A practical and highly regio- and stereoselective synthesis of oligoprenols starting from commercially available geraniol is described. The convergent synthetic strategy features the iterative allyl-allyl coupling of monomers easily derived from geraniol that contain one reacting terminal functional group and the repetitive reductive elimination of the p-toluenesulfonyl (Ts) groups.
- Yu, Xiong-Jie,Zhang, Hao,Xiong, Fang-Jun,Chen, Xu-Xiang,Chen, Fen-Er
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experimental part
p. 1967 - 1974
(2009/02/07)
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- Enzymatic formation of pyrrole-containing novel cyclic polyprenoids by bacterial squalene:hopene cyclase
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A convergent synthesis provided two pyrrole-containing squalene analogues, in which a C20 isoprene unit is connected to pyrrole, 2-(geranylgeranyl)pyrrole and 2-(farnesyldimethylallyl)pyrrole. When incubated with recombinant squalene:hopene cyclase from Alicyclobacillus acidocaldarius, 2-(farnesyldimethylallyl)pyrrole was enzymatically converted to a 10:1 mixture of a tricyclic and a bicyclic unnatural novel polyprenoids, whereas 2-(geranylgeranyl)pyrrole was not a substrate for the enzyme.
- Tanaka, Hideya,Noma, Hisashi,Noguchi, Hiroshi,Abe, Ikuro
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p. 3085 - 3089
(2007/10/03)
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- Synthesis and antimycobacterial activity of agelasine E and analogs
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Agelasine E, previously isolated from the marine sponge Agelas nakamurai, has been synthesized for the first time, together with analogs with various terpenoid side chains. Treatment of N6-methoxy-9-methyl-9H-purin-6- amine with allylic bromides gave the desired 7,9-dialkylpurinium salts together with minor amounts of the N6-alkylated isomer. The N 6-methoxy group was finally removed reductively. 1H- 15N HMBC and 1H-15N HSQC NMR spectroscopy gave additional information on tautomerism and charge delocalization in the purine derivatives studied. The heterocyclic products were screened for activity against Mycobacterium tuberculosis and agelasine analogs carrying a relatively long terpenoid substituent in the purine 7-position and a methoxy group at N-6 were potent inhibitors of bacterial growth. Since agelasine analogs with the geranylgeranyl chain at N-7 exhibited antimicrobial activity, several strategies for synthesis of geometrically pure (2E,6E,10E)-geranylgeranyl bromide from geranyllinalool were evaluated. The Royal Society of Chemistry 2005.
- Bakkestuen, Anne Kristin,Gundersen, Lise-Lotte,Petersen, Dirk,Utenova, Bibigul T.,Vik, Anders
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p. 1025 - 1033
(2007/10/03)
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- Enzymatic formation of indole-containing unnatural cyclic polyprenoids by bacterial squalene:hopene cyclase
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(Chemical Equation Presented) Two indole-containing substrate analogues, in which a C20 isoprene unit is connected to indole (3-(geranylgeranyl)indole and 3-(farnesyldimethylallyl)indole), were synthesized and tested for enzymatic cyclization by squalene:hopene cyclase from Alicyclobacillus acidocaldarius. Interestingly, 3-(geranylgeranyl)indole was not a substrate for the bacterial squalene cyclase, while 3-(farnesyldimethylallyl) indole was efficiently converted to a 2:1 mixture of unnatural novel products.
- Tanaka, Hideya,Noguchi, Hiroshi,Abe, Ikuro
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p. 5873 - 5876
(2007/10/03)
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- Squalene-hopene cyclase: Insight into the role of the methyl group on the squalene backbone upon the polycyclization cascade. Enzymatic cyclization products of squalene analogs lacking a 26-methyl group and possessing a methyl group at C(7) or C(11)
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To provide deep insight into the polycyclization reaction of squalene, some analogs were synthesized and incubated with the cell-free homogenates of the recombinant Escherichia coli encoding the wild-type squalene cyclase. The presence of C(6)-Me leads to an efficient polycyclization cascade. Substitution of the C(14)-H and the C(18)-H with a methyl group halted the polycylization reaction at the tricyclic ring stage having a 6/6/6-fused ring system and the tetracycle with a 6/6/6/6-fused ring, respectively, both of which were produced according to a Markovnikov closure. Replacement of the C(7)-H and the C(11)-H with a methyl group led to no cyclization. These results, in conjunction with our previous reports, indicated that the methyl positions are important for bringing to completion of the normal polycylization reaction and further demonstrated that the precise steric bulk size at the methyl positions of squalene is critical to the correct folding and the strong binding of the substrate to the squalene cyclase.
- Nakano, Shin-Ichi,Ohashi, Shumi,Hoshino, Tsutomu
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p. 2012 - 2022
(2007/10/03)
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- A photoactivatable prenylated cysteine designed to study isoprenoid recognition
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Protein prenylation, involving the alkylation of a specific C-terminal cysteine with a C15 or C20 isoprenoid unit, is an essential posttranslational modification required by most GTP-binding proteins for normal biological activity. Despite the ubiquitous nature of this modification and numerous efforts aimed at inhibiting prenylating enzymes for therapeutic purposes, the function of prenylation remains unclear. To explore the role the isoprenoid plays in mediating protein-protein recognition, we have synthesized a photoactivatable, isoprenoid-containing cysteine analogue (2) designed to act as a mimic of the C-terminus of prenylated proteins. Photolysis experiments with 2 and RhoGDI (GDI), a protein which interacts with prenylated Rho proteins, suggest that the GDI is in direct contact with the isoprenoid moiety. These results, obtained using purified GDI as well as Escherichia coli (E. coli) crude extract containing GDI, suggest that this analogue will be an effective and versatile tool for the investigation of putative isoprenoid binding sites in a variety of systems. Incorporation of this analogue into peptides or proteins should allow for even more specific interactions between the photoactivatable isoprenoid and any number of isoprenoid binding proteins.
- Kale,Raab,Yu,Dean,Distefano
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p. 4373 - 4381
(2007/10/03)
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- Synthesis of rac-hippospongic acid A and revision of the structure
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rac-Hippospongic acid A of the reported structure 1 and the revised structure 2 were synthesized. The synthetic strategy of these compounds consists of homologation of (2E,6E,10E)-geranylgeraniol and (2E,6E)-farnesol, respectively, Wadsworth-Emmons reaction, and cyclization to form the tetrahydropyran ring bearing an α-methylene group on the carboxylic moiety. Spectral comparisons of the synthetic compounds 1,2 and the natural product suggested that hippospongic acid A bears the structure of 2.
- Tokumasu, Munetaka,Ando, Hiroshi,Hiraga, Yoshikazu,Kojima, Satoshi,Ohkata, Katsuo
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p. 489 - 496
(2007/10/03)
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- Superacidic low temperature cyclization of terpenylphenyisulfones
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The superacidic cyclization of aliphatic and partially cyclized C10- C20 terpenylphenylsulfones proceeds structure-selectively and stereospecifically, affording α- or mixtures of α- and γ-isomers of completely cyclized terpenylphenylsulfones. The configuration of the phenylsuffonylmethylene group in the cyclized products is predetermined by the configuration of the allylic double bond in the starting compounds.
- Kulcitki, Veaceslav,Ungur, Nicon,Vlad, Pavel F.
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p. 11925 - 11934
(2007/10/03)
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- The substrate specificity of tocopherol cyclase
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The substrate specificity of the enzyme tocopherol cyclase from the blue-green algae Anabaena variabilis (Cyanobacteria) was investigated with 11 substrate analogues revealing the significance of three major recognition sites: (i) the OH group at C(1) of the hydroquinone, (ii) the (E) configuration of the double bond, and (iii) the length of the lipophilic side chain. Experiments with two affinity matrices suggest that substrates approach the enzyme's active site with the hydrophobic tail.
- Stocker, Achim,Fretz, Heinz,Frick, Haroun,Ruettimann, August,Woggon, Wolf-Dietrich
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p. 1129 - 1134
(2007/10/03)
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- Polyisoprene compounds and salts thereof
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There are given disclosures on a polyisoprene compound of the formula STR1 wherein Y is S, O, NH or STR2 l is an integer of 2-10, Z is a group of STR3 R1 and R2 are same or different and each means a hydrogen atom or an alkyl group having C1-4, m is an integer of 0 or 1, and n is an integer of 0, 1 or 2, a salt thereof, a process for the preparation of same, and use thereof.
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- Selective 1,5-Diene Synthesis. A Radical Approach
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A new synthetic route to 1,5-dienes is described.Irradiation of a mixture of allyl bromides and allyl sulfides in the presence of hexamethylditin gives the cross-coupled products selectively.
- Yanagisawa, Akira,Noritake, Yoshiyuki,Yamamoto, Hisashi
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p. 1899 - 1902
(2007/10/02)
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- Stereoselective Synthesis of Solanesol and all-trans-Decaprenol
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Allylic p-tolyl sulphonates (5), (14), and (16) couple with allylic bromide (7) and geranyl bromide to produce regio- and stereo-chemically pure 1,5-diene systems.The coupling of all-trans-ω-bromogeranyl acetate (7) with geranyl p-tolyl sulphone (5) and higher isoprenologues (21), (24), and (27), followed by reductive elimination of p-tolylsulphonyl group, furnishes a stereoselective synthesis of all-trans-polyprenols (3), (23), (26), and decaprenol (1b).Solanesol (1a) was synthesised using trans-4-chloroprenyl acetate (29) instead of (7).
- Sato, Kikumasa,Inoue, Seiichi,Onishi, Akira,Uchida, Nobuhiko,Minowa, Nobuto
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p. 761 - 769
(2007/10/02)
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- Structure and Biosynthesis of Cleomeprenols from the Leaves of Cleome spinosa
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Cleomeprenols isolated from Cleome spinosa L. (Capparidaceae) have been identified as nonaprenol (1), decaprenol (2), and undecaprenol (3), which are composed of an ω-terminal isoprene, three internal E-isoprene, and the remaining Z-isoprene residues, respectively.Feeding experiments using stereospecifically double-labelled radioactive mevalonate showed that all the cleomeprenols are composed of four biogenetically E- and the remaining biogenetically Z-isoprene residues.Occurence of the succesive cis-condensation of isoprene residues with (2E,6E,10E)-geranylgeranyl pyrophosphate was demonstrated by comparing the incorporation of a homologue of all-E-prenyl pyrophosphates with that of the corresponding 2Z-isomer.
- Suga, Takayuki,Shishibori, Tsuyoshi
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p. 2098 - 2104
(2007/10/02)
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