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Search for "ATP" in Full Text gives 80 result(s) in Beilstein Journal of Organic Chemistry.
Thermodynamic and kinetic stabilization of divanadate in the monovanadate/divanadate equilibrium using a Zn-cyclene derivative: Towards a simple ATP synthase model
- Hanno Sell,
- Anika Gehl,
- Frank D. Sönnichsen and
- Rainer Herges
Beilstein J. Org. Chem. 2012, 8, 81–89, doi:10.3762/bjoc.8.8
- Hanno Sell Anika Gehl Frank D. Sonnichsen Rainer Herges Otto-Diels Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Otto-Hahn-Platz 4, 24418 Kiel, Germany 10.3762/bjoc.8.8 Abstract For the condensation of anions such as phosphate and ADP to form ATP and water, nature
- ; Introduction Driving endergonic reactions with external energy sources is one of the challenging and so far unsolved problems in supramolecular chemistry. The best known example in nature is probably the condensation of phosphate and ADP to ATP, driven by a proton gradient across a membrane [1]. There are a
- number of preconditions that have to be met for such an energy driven condensation of inorganic anions. At least three steps (four stages) are required (Figure 1): a) Moving both complexated anions together, b) bond formation (condensation), and c) product release/reactant binding. In the ATP synthase
Graphical Abstract
Figure 1: Simplified free energy scheme for driving an endergonic condensation (elimination/addition of water...
Figure 2: Binding motive of a vanadate zinc benzylcyclene complex (left) as suggested by the results of DFT c...
Figure 3: 51V NMR titration at pH 9.5 ([V]t = 1.5 mM, [1]t = 0 to 7.5 mM (0 to 5 equiv), 100 mM CHES). [V]t a...
Figure 4: Speciation of vanadium in a solution containing 1.5 mM Na3VO4, 100 mM CHES (pH = 9.5) and a Zn-benz...
Figure 5: 51V EXSY NMR spectrum (tmix = 1 ms) of a solution containing 1.5 mM Na3VO4, 3 mM Zn-benzylcyclene a...
Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes
- Jan-Christoph Kehr,
- Douglas Gatte Picchi and
- Elke Dittmann
Beilstein J. Org. Chem. 2011, 7, 1622–1635, doi:10.3762/bjoc.7.191
- studied, PatD is a single ATP-dependent enzyme not requiring an additional oxidase enzyme [60]. The PatG protease encoded by the cluster was shown to macrocyclize diverse substrates by a mechanism closely resembling the thioesterase-catalyzed chemistry of most NRPS systems [61]. Several related pathways
- Microcystis and Planktothrix [64][65]. Post-translational modification of microviridins is achieved by the activity of two closely related ATP grasp ligases, MdnB and MdnC (MvdC and D in Planktothrix). The enzymes introduce two ω-ester linkages between threonine and aspartate and serine and glutamate (MdnC
- MAA shinorine in Anabaena variabilis ATCC 29413: A dehydroquinase synthase homologue (DHQS), an O-methyl-transferase (O-MT), an ATP grasp ligase and an NRPS-like enzyme. Cloning of the entire gene cluster in E. coli led to the production of shinorine. The production of the intermediate 4-deoxygadusol
Graphical Abstract
Figure 1: Cyanobacteria proliferate in diverse habitats. A) Bloom-forming freshwater cyanobacteria of the gen...
Figure 2: Schematic representation of enzymatic domains in A) nonribosomal peptide synthetases (NRPS); B) pol...
Figure 3: Structures of NRPS and PKS products in freshwater cyanobacteria.
Figure 4: A) Synthesis of the Adda ((2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic...
Figure 5: Structures of NRPS and PKS products in marine cyanobacteria.
Figure 6: A) Formation of the trichloroleucyl starter unit of barbamide (7) synthesis through the non-heme ir...
Figure 7: Structures of NRPS and PKS products in terrestrial cyanobacteria.
Figure 8: Synthesis of the (2S,4S)-4-methylproline moiety of nostopeptolides A (13).
Figure 9: Structures of cyanobacterial peptides that are synthesized ribosomally and post-translationally mod...
Figure 10: Formation of ester linkages and ω-amide linkage in microviridins 17 by the ATP grasp ligases MvdD a...
Figure 11: Structures of cyanobacterial sunscreen compounds.
Coupled chemo(enzymatic) reactions in continuous flow
- Ruslan Yuryev,
- Simon Strompen and
- Andreas Liese
Beilstein J. Org. Chem. 2011, 7, 1449–1467, doi:10.3762/bjoc.7.169
- of ATP and glucose 1-phosphate. When the reaction mixture containing starting materials and cofactors was circulated for 48 hours through the reactor, 50% of UMP was transformed to UDP-Gal. Although in their work the authors did not establish the continuous production of UDP-Gal, in principle such a
Graphical Abstract
Figure 1: Metabolic pathways in a living cell as an example of efficient coupled-reaction processes. A: Subst...
Figure 2: Four generations of biotransformations. I: Single-reaction processes; II: Single-reaction processes...
Scheme 1: Production of L-leucine (3) in a continuously operating enzyme membrane reactor (EMR). E1: L-Leucin...
Scheme 2: Production of D-mandelic acid (5) in a continuously operating enzyme membrane reactor. E1: D-(−)-Ma...
Scheme 3: Simultaneous synthesis of gluconic acid (9) and glutamic acid (8) in a continuously operated membra...
Scheme 4: Production of L-tert-leucine (11) in a continuously operated enzyme membrane reactor equipped with ...
Scheme 5: Continuous oxidation of lactose (12) to lactobionic acid (13) in a dynamic membrane-aerated reactor...
Scheme 6: Production of N-acetylneuraminic acid (17) in a continuously operated enzyme membrane reactor. E1: ...
Scheme 7: Chemo-enzymatic epoxidation of 1-methylcyclohexene (18) in a packed-bed reactor (PBR) containing No...
Scheme 8: Continuous production of (R)-1-phenylethyl propionate (24) by dynamic kinetic resolution of (rac)-1...
Scheme 9: Synthesis of D-xylulose (28) from D,L-serine (26) and D,L-glyceraldehyde (25) in a continuously ope...
Scheme 10: Continuous production of L-alanine (31) from fumarate (29) in a two-stage enzyme membrane reactor. ...
Scheme 11: Continuous synthesis of 1-phenyl-(1S,2S)-propanediol (35) in a cascade of two enzyme membrane react...
Scheme 12: Production of a dipeptide 39 in a cascade of two continuously operated membrane reactors. E1: Carbo...
Scheme 13: Continuous production of GDP-mannose (43) from mannose 1-phosphate (40) in a cascade of two enzyme ...
Scheme 14: Continuous solvent-free chemo-enzymatic synthesis of ethyl (S)-3-(benzylamino)butanoate (48) in a s...
Scheme 15: Continuous chemo-enzymatic synthesis of grossamide (52) in a cascade of packed-bed reactors. E: Per...
Scheme 16: Chemo-enzymatic synthesis of 2-aminophenoxazin-3-one (56) in a cascade of continuously operating pa...
Scheme 17: Continuous conversion of 3-phospho-D-glycerate (57) into D-ribulose 1,5-bisphosphate (58) in a casc...
Scheme 18: Continuous hydrolysis of 4-cyanopyridine (59) to isonicotinic acid (61) in a cascade of two packed-...
Scheme 19: Continuous fermentative production of ethanol (64) from hardwood lignocellulose (62) in a stirred-t...
Scheme 20: Production of hydrogen by anaerobic fermentation of glucose (7) using Clostridium acetobutylicum ce...
Scheme 21: Continuous production of (2R,5R)-hexanediol (67) in an enzyme membrane reactor containing whole cel...
Scheme 22: Synthesis of L-phenylalanine (69) in a continuously stirred tank reactor equipped with a hollow-fib...
Scheme 23: Continuous epoxidation of 1,7-octadiene (70) to (R)-7-epoxyoctene (72) by a strain of Pseudomonas o...
Scheme 24: Oxidation of styrene (73) to (S)-styrene oxide (74) in a continuously operated biofilm tube reactor...
Scheme 25: Reduction of estrone (75) to β-estradiol (76) by Saccharomyces cerevisiae in a cascade of two stirr...
Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid
- Arne Homann,
- Riaz-ul Qamar,
- Sevnur Serim,
- Petra Dersch and
- Jürgen Seibel
Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24
- kinase; ATP: adenosine triphosphate; PEP: phosphoenolpyruvate; CTP: cytidine triphosphate; PPi: pyrophosphate; DNA: deoxyribonucleic acid; mRNA: messenger ribonucleic acid. Proposed metabolic pathway of Neu5Hex 3 based on known mechanisms of Neu5Gc 2 uptake [5]. TGN: trans-Golgi network, CMP: cytidine
Graphical Abstract
Scheme 1: The natural forms of sialic acids, human N-acetylneuraminic acid (Neu5Ac, 1) and mammalian N-glycol...
Scheme 2: Synthesis of N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex 3).
Scheme 3: Metabolic pathway of Ac4GlcNAz and the genetic control of Neu5Ac 1 synthesis by feedback inhibition...
Scheme 4: Proposed metabolic pathway of Neu5Hex 3 based on known mechanisms of Neu5Gc 2 uptake [5]. TGN: trans-G...
Scheme 5: Labelling of alkynylated neuraminic acid by azido-fluorescein.
Figure 1: Top left: HEp-2 cells incorporated with Ac4GlcNAz 16, labelled with alkynylated TAMRA at 580 nm. Bo...
Recent progress on the total synthesis of acetogenins from Annonaceae
- Nianguang Li,
- Zhihao Shi,
- Yuping Tang,
- Jianwei Chen and
- Xiang Li
Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48
- ]. Inhibition by these mechanisms results in adenosine triphosphate (ATP) deprivation, which leads to apoptosis of the highly energy demanding tumor cells [11]. The acetogenins are now considered as the most potent (effective in nanomolar concentrations) known inhibitors of the mitochondrial complex I [9][12
Graphical Abstract
Scheme 1: Total synthesis of longifolicin by Marshall’s group.
Scheme 2: Total synthesis of corossoline by Tanaka’s group.
Scheme 3: Total synthesis of corossoline by Wu’s group.
Scheme 4: Total synthesis of pseudo-annonacin A by Hanessian’s group.
Scheme 5: Total synthesis of tonkinecin by Wu’s group.
Scheme 6: Total synthesis of gigantetrocin A by Shi’s group.
Scheme 7: Total synthesis of annonacin by Wu’s group.
Scheme 8: Total synthesis of solamin by Kitahara’s group.
Scheme 9: Total synthesis of solamin by Mioskowski’s group.
Scheme 10: Total synthesis of cis-solamin by Makabe’s group.
Scheme 11: Total synthesis of cis-solamin by Brown’s group.
Scheme 12: The formal synthesis of (+)-cis-solamin by Donohoe’s group.
Scheme 13: Total synthesis of cis-solamin by Stark’s group.
Scheme 14: Total synthesis of mosin B by Tanaka’s group.
Scheme 15: Total synthesis of longicin by Hanessian’s group.
Scheme 16: Total synthesis of murisolin and 16,19-cis-murisolin by Tanaka’s group.
Scheme 17: Synthesis of a stereoisomer library of (+)-murisolin by Curran’s group.
Scheme 18: Total synthesis of murisolin by Makabe’s group.
Scheme 19: Total synthesis of reticulatain-1 by Makabe’s group.
Scheme 20: Total synthesis of muricatetrocin C by Ley’s group.
Scheme 21: Total synthesis of (4R,12S,15S,16S,19R,20R,34S)-muricatetrocin (146) and (4R,12R,15S,16S,19R,20R,34S...
Scheme 22: Total synthesis of parviflorin by Hoye’s group.
Scheme 23: Total synthesis of parviflorin by Trost’s group.
Scheme 24: Total synthesis of trilobacin by Sinha’s group.
Scheme 25: Total synthesis of 15-epi-annonin I 181b by Scharf’s group.
Scheme 26: Total synthesis of squamocin A and squamocin D by Scharf’s group.
Scheme 27: Total synthesis of asiminocin by Marshall’s group.
Scheme 28: Total synthesis of asiminecin by Marshall’s group.
Scheme 29: Total synthesis of (+)-(30S)-bullanin by Marshall’s group.
Scheme 30: Total synthesis of uvaricin by the group of Sinha and Keinan.
Scheme 31: Formal synthesis of uvaricin by Burke’s group.
Scheme 32: Total synthesis of trilobin by Marshall’s group.
Scheme 33: Total synthesis of trilobin by the group of Sinha and Keinan.
Scheme 34: Total synthesis of asimilobin by the group of Wang and Shi.
Scheme 35: Total synthesis of squamotacin by the group of Sinha and Keinan.
Scheme 36: Total synthesis of asimicin by Marshall’s group.
Scheme 37: Total synthesis of asimicin by the group of Sinha and Keinan.
Scheme 38: Total synthesis of asimicin by Roush’s group.
Scheme 39: Total synthesis of asimicin by Marshall’s group.
Scheme 40: Total synthesis of 10-hydroxyasimicin by Ley’s group.
Scheme 41: Total synthesis of asimin by Marshall’s group.
Scheme 42: Total synthesis of bullatacin by the group of Sinha and Keinan.
Scheme 43: Total synthesis of bullatacin by Roush’s group.
Scheme 44: Total synthesis of bullatacin by Pagenkopf’s group.
Scheme 45: Total synthesis of rollidecins C and D by the group of Sinha and Keinan.
Scheme 46: Total synthesis of 30(S)-hydroxybullatacin by Marshall’s group.
Scheme 47: Total synthesis of uvarigrandin A and 5(R)-uvarigrandin A by Marshall’s group.
Scheme 48: Total synthesis of membranacin by Brown’s group.
Scheme 49: Total synthesis of membranacin by Lee’s group.
Scheme 50: Total synthesis of rolliniastatin 1 and rollimembrin by Lee’s group.
Scheme 51: Total synthesis of longimicin D by the group of Maezaki and Tanaka.
Scheme 52: Total synthesis of the structure proposed for mucoxin by Borhan’s group.
Scheme 53: Modular synthesis of adjacent bis-THF annonaceous acetogenins by Marshall’s group.
Scheme 54: Total synthesis of 4-deoxygigantecin by Tanaka’s group.
Scheme 55: Total synthesis of squamostatins D by Marshall’s group.
Scheme 56: Total synthesis of gigantecin by Crimmins’s group.
Scheme 57: Total synthesis of gigantecin by Hoye’s group.
Scheme 58: Total synthesis of cis-sylvaticin by Donohoe’s group.
Scheme 59: Total synthesis of 17(S),18(S)-goniocin by Sinha’s group.
Scheme 60: Total synthesis of goniocin and cyclogoniodenin T by the group of Sinha and Keinan.
Scheme 61: Total synthesis of jimenezin by Takahashi’s group.
Scheme 62: Total synthesis of jimenezin by Lee’s group.
Scheme 63: Total synthesis of jimenezin by Hoffmann’s group.
Scheme 64: Total synthesis of muconin by Jacobsen’s group.
Scheme 65: Total synthesis of (+)-muconin by Kitahara’s group.
Scheme 66: Total synthesis of muconin by Takahashi’s group.
Scheme 67: Total synthesis of muconin by the group of Yoshimitsu and Nagaoka.
Scheme 68: Total synthesis of mucocin by the group of Sinha and Keinan.
Scheme 69: Total synthesis of mucocin by Takahashi’s group.
Scheme 70: Total synthesis of (−)-mucocin by Koert’s group.
Scheme 71: Total synthesis of mucocin by the group of Takahashi and Nakata.
Scheme 72: Total synthesis of mucocin by Evans’s group.
Scheme 73: Total synthesis of mucocin by Mootoo’s group.
Scheme 74: Total synthesis of (−)-mucocin by Crimmins’s group.
Scheme 75: Total synthesis of pyranicin by the group of Takahashi and Nakata.
Scheme 76: Total synthesis of pyranicin by Rein’s group.
Scheme 77: Total synthesis of proposed pyragonicin by the group of Takahashi and Nakata.
Scheme 78: Total synthesis of pyragonicin by Rein’s group.
Scheme 79: Total synthesis of pyragonicin by Takahashi’s group.
Scheme 80: Total synthesis of squamostanal A by Figadère’s group.
Scheme 81: Total synthesis of diepomuricanin by Tanaka’s group.
Scheme 82: Total synthesis of (−)-muricatacin [(R,R)-373a] and its enantiomer (+)-muricatacin [(S,S)-373b] by ...
Scheme 83: Total synthesis of epi-muricatacin (+)-(S,R)-373c and (−)-(R,S)-373d by Scharf’s group.
Scheme 84: Total synthesis of (−)-muricatacin 373a and 5-epi-(−)-muricatacin 373d by Uang’s group.
Scheme 85: Total synthesis of four stereoisomers of muricatacin by Yoon’s group.
Scheme 86: Total synthesis of (+)-muricatacin by Figadère’s group.
Scheme 87: Total synthesis of (+)-epi-muricatacin and (−)-muricatacin by Couladouros’s group.
Scheme 88: Total synthesis of muricatacin by Trost’s group.
Scheme 89: Total synthesis of (−)-(4R,5R)-muricatacin by Heck and Mioskowski’s group.
Scheme 90: Total synthesis of muricatacin (−)-373a by the group of Carda and Marco.
Scheme 91: Total synthesis of (−)- and (+)-muricatacin by Popsavin’s group.
Scheme 92: Total synthesis of (−)-muricatacin by the group of Bernard and Piras.
Scheme 93: Total synthesis of (−)-muricatacin by the group of Yoshimitsu and Nagaoka.
Scheme 94: Total synthesis of (−)-muricatacin by Quinn’s group.
Scheme 95: Total synthesis of montecristin by Brückner’s group.
Scheme 96: Total synthesis of (−)-acaterin by the group of Franck and Figadère.
Scheme 97: Total synthesis of (−)-acaterin by Singh’s group.
Scheme 98: Total synthesis of (−)-acaterin by Kumar’s group.
Scheme 99: Total synthesis of rollicosin by Quinn’s group.
Scheme 100: Total synthesis of Rollicosin by Makabe’s group.
Scheme 101: Total synthesis of squamostolide by Makabe’s group.
Scheme 102: Total synthesis of tonkinelin by Makabe’s group.
