A method was developed for the large-scale bioconversion of novel 6-deoxyerythronolide B (6-dEB) analogs into erythromycin analogs. Erythromycin biosynthesis in Saccharopolyspora erythraea proceeds via the formation of a polyketide aglycone, 6-dEB, which is subsequently glycosylated, hydroxylate...
The synthesis of 6-deoxyerythronolide B (1) has been completed using the β-ketoimide dipropionyl building block 2 in the synthesis of the C1C7 and C8C15 subunits. A convergent double stereodifferentiating Mukaiyama aldol coupling reaction, a biomimetic deoxygenation, and a high-yield macroc...
The critical role of protein–protein interactions in the chemistry of polyketide synthases is well established. However, the transient and weak nature of these interactions, in particular those involving the acyl carrier protein (ACP), has hindered efforts to structurally characterize these int...
Incubation of chirally deuterated NADPH with 6-deoxyerythronolide B synthase (DEBS) modules 5 and module 6 and analysis of the derived triketide lactones established that the two ketoreductase domains, KR5 and KR6, are both specific for the 4-pro-S hydride of the nicotinamide cofactor.
A novel variant of 6-deoxyerythronolide B synthase (DEBS) module 2 was constructed to explore the balance between protein–protein-mediated intermodular channeling and intrinsic substrate specificity within DEBS. This construct, termed (N3)Mod2 + TE, was co-incubated with a complementary, donor ...
Feeding of synthetic precursors to a blocked mutant of 6-deoxyerythronolide B synthase (DEBS) [1] led to production of novel 6-deoxyerythronolide B analogs in vivo containing additional non-natural oxygen substituents as well as additional reactive groups.
A robust high cell-density fed-batch bioprocess was developed for the heterologous production of 6-deoxyerythronolide B (6-dEB), the macrocyclic core of the antibiotic erythromycin, with a recombinant Escherichia coli strain expressing the 6-deoxyerythronolide B synthase (DEBS) from Saccharopoly...
Chromosomal engineering was used to localize the deoxyerythronolide B synthase (DEBS) genes and propionyl-CoA carboxylase (PCC) genes to the BAP1 Escherichia coli chromosome creating the new strain YW9. YW9 then featured a plasmid-free heterologous pathway for the production of the polyketide pr...
The 6-deoxyerythronolide B synthase (DEBS) is a prototypical assembly line polyketide synthase produced by the actinomycete Saccharopolyspora erythraea that synthesizes the macrocyclic core of the antibiotic erythromycin 6-deoxyerythronolide B. The megasynthase is a 2-MDa trimeric complex compos...
The photochemical [2 + 2] cycloadditions (the so-called Paternò-Büchi (PB) reaction) of 1,3-dimethyluracil (DMU) and 1,3-dimethylthymine (DMT) with benzophenone (1d) and its derivatives (BPs) with 4,4′-disubstituted groups including CH3O (1a), CH3 (1b), t-Bu (1c), F (1e), Cl (1f) and CN (1g) ...
This study aims at investigating the cytotoxicity and some of the modes of action of 3,5-bis(3-dimethylamino-4-hydroxybenzylidene)-4-piperidone trihydrochloride 3 and two related compounds 2 (which lacks the dimethylaminomethyl groups) and 4 (which has an additional dimethylaminoethyl substituen...
A new benzohydrazone compound N′-(3-bromo-2-hydroxybenzylidene)-4-methoxybenzohydrazide (H2L) was prepared. Reaction of H2L and acetohydroxamic acid (HAHA) with VO(acac)2 in methanol gave the complex [VOL(AHA)]. Both H2L and the oxovanadium complex were characterized by elemental analysis, IR, ...
Two new oxidovanadium(V) complexes, [VOLL1] and [VOLL2], where L is the dianionic form of N′-(3-ethoxy-2-hydroxybenzylidene)-3-methylbenzohydrazide (H2L), L1 is maltolatel, and L2 is ethylmaltolate, have been prepared. Both H2L and the complexes have been characterized by elemental analysis, IR...
The single crystal of (E)-N-(3-Methoxy-4-hydroxybenzylidene)-4-nitrobenzohydrazide monohydrate (MHBNB) was grown by a slow evaporation method. The crystal structure was determined by single crystal X-ray diffraction method. The electron density, Hirshfeld surface and fingerprint analysis reveals...
The reactions of the Schiff base ligand (E)-4-chloro-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide (L) with substituted dibenzyltin dichlorides yielded a series of monobenzyltin complexes with the general formula (RC7H6)Sn(L)(S)Cl, where R = p-CH3, p-Cl, H, p-F, p-Br, o-CH3, o-F and S = H2O...
Two new amido-bridged complexes, dimeric [MnIII(L)(H2O)]2·6H2O (1), and two-dimensional (2D) [K(MeOH)2MnIIICuII(L)2] (2) (H3L = 1-(2-hydroxybenzamido)-2-((2-hydroxy-3-methoxybenzylidene)amino)ethane) have been prepared and characterized by X-ray single-crystal structure analysis and magnetic me...
Three new diorganotin(IV) complexes of the general formula R2Sn[3-(OMe)-2-OC6H3CHN–NC(O)Ph] (R = Ph, Ia; R = Me, Ib; R = n-Bu, Ic) have been synthesised from the corresponding diorganotin(IV) dichlorides and the ligand, N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide in methanol at room temp...
The action of (Z)-N-(2-bromo-5-hydroxy-4-methoxybenzylidene)-2-methylpropan-2-amine oxide (RP6) on rat cortical neurons in culture, under oxygen–glucose-deprivation conditions, is reported. Cortical neurons in culture were treated during 1 h with OGD. After, they were placed under normal condit...
A novel fluorescent chemodosimeter, 1-(2-methoxybenzylidene)-4-phenylthiolsemicarbazide, was studied. In 90:10 (v/v) mixture of CH3CN and water binary solution, it exhibits high selectivity toward Cu2+ but very low response toward other competitive cations. The Cu2+ promoting cyclization of the ...
On the basis of the structures of serotonin modulators or drugs (NAN-190, buspirone, aripiprazole) and phosphodiesterase 4 (PDE4) inhibitors (rolipram, RO-20-1724), a series of novel multitarget 5-arylidenehydantoin derivatives with arylpiperazine fragment was synthesized. Among these compounds,...
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