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Search for "chemoenzymatic synthesis" in Full Text gives 27 result(s) in Beilstein Journal of Organic Chemistry.
Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus
Beilstein J. Org. Chem. 2024, 20, 815–822, doi:10.3762/bjoc.20.73
- findings from both the heterologous expression and substrate spectrum analysis indicate the particular affinity of CavA for the C-3 position, which might be used for chemoenzymatic synthesis of C-3 hydroxylated drimanyl meroterpenoids using drimenol and its analogues as substrates. However, it is important
- efficient chemoenzymatic synthesis of DMTs or drimanyl indoles [44]. (a) Representative bioactive drimane-type sesquiterpenoids (DMTs). (b) Reported biosynthetic pathways of DMTs from fungi. Chemical structures and HPLC analysis. (a) Chemical structures of isolated sesquiterpenes 2–4 from S. clavuligerus
Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization
Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66
- , and their hybrids, thioesterase (TE) domains play a significant role in late-stage macrocyclization. These domains can accept mimics of native substrates in vitro and exhibit potential for use in total synthesis. This review summarizes the recent advances of TE domains in the chemoenzymatic synthesis
- for these natural products that aim to address the common issues in classical synthetic approaches and increase synthetic efficiencies, which have the potential to facilitate further pharmaceutical research. Keywords: biosynthesis; chemoenzymatic synthesis; macrocyclic peptides; macrocyclic
- peptides and even small proteins. In the chemoenzymatic synthesis of macrocyclic peptides, SPPS strategies provide highly efficient routes to access linear precursors, accelerating the development of enzymatic macrocyclization. The tyrocidines Tyrocidine A (1), a cyclic decapeptide isolated from Bacillus
Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway
Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1
- ) within 1 h. This property is probably due to the high stability of CmaA6. The high activity of CmaA6 makes it a useful tool for biochemical experiments and chemoenzymatic synthesis. Indeed, the discovery of CmaA6 allowed us to analyze the kinetics of the denitrification reaction catalyzed by AvaA7, which
Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase
Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142
- pathogen in these cases is mucoid Pseudomonas aeruginosa. Such infections are characterised by overproduction of the exopolysaccharide alginate. We present herein the design and chemoenzymatic synthesis of sugar nucleotide tools to probe a critical enzyme within alginate biosynthesis, GDP-mannose
Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants
Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135
- [7]. Hence, there is considerable interest in CYPs involved in triterpenoid and steroid metabolism in plants not only for improving our understanding of plant specialised metabolism, but also for synthetic biology and chemoenzymatic synthesis. In this review, we will provide an extensive overview of
Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli
Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89
- group or a combination of enzymatic and chemical tools (chemoenzymatic synthesis) [8][9][10][11]. Despite great efforts spanning several decades, de novo organic synthetic methods access to the core diterpene skeletons are still highly challenging owing to their numerous chiral centers and polycyclic
- opioid receptor), oridonin (cytotoxic), and gibberellin (phytohormone) (Figure 1b) [24][25][26][27]. How to efficiently construct the core carbon skeletons is a critical question in utilizing the advanced ‘two-phase strategy’ or chemoenzymatic synthesis to readily synthesize clerodane and ent-kaurane
Structural basis for endoperoxide-forming oxygenases
Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71
- reductants. In this aspect, the chemoenzymatic synthesis would be a useful approach to synthesize endoperoxide-containing compounds with high regio- and stereoselectivities. The structural and mechanistic analyses of the enzymes for endoperoxide formation reviewed here would provide useful information about
Progress and challenges in the synthesis of sequence controlled polysaccharides
Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129
- overcome some limitations of the individual methods, a combination of methods is sometimes exploited. A classic example is chemoenzymatic synthesis, in which synthetic BBs are employed to direct the enzymatic synthesis towards the desired polysaccharide target. In this review, we discuss the recent efforts
- substitution. A collection of linear β(1–4)-ᴅ-xylan chains and with α(1–3)-ʟ-arabinofuranosyl branches was quickly assembled to identify the binding epitopes of monoclonal antibodies. These oligomers, together with other well-defined analogues obtained by chemoenzymatic synthesis, were converted to the
Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols
Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52
- toxic oxidants. Keywords: chemoenzymatic synthesis; cortisol; hydroxylation; secosterol; whole-cell catalysis; Introduction Developments in the chemistry of steroids have stimulated extensive research interest in the exploration of new synthetic methods since the 1960s. Advances in synthetic biology
- total synthesis sequence. Inspired by several enzymatic oxidations [22][23][24][25], we envisioned to carry out oxidation at C9 in an environmentally benign way using an oxidation by a whole-cell biocatalysis method. The first, and so far the only chemoenzymatic synthesis of 9,11-secosterols using
Regioselective chemoenzymatic syntheses of ferulate conjugates as chromogenic substrates for feruloyl esterases
Beilstein J. Org. Chem. 2021, 17, 325–333, doi:10.3762/bjoc.17.30
- that obviates the need for a glycosyl moiety while containing a cleavable hydroxylated linker that mimics the natural geometry and physicochemical properties of glycosidic linkages. Results and Discussion Chemoenzymatic synthesis of 5-O-feruloylated α-ʟ-arabinofuranosides The synthesis of the
- during the colorimetric assays. + and − indicate whether the reaction conditions (e.g., pH > 10 or the addition of ethylene) were satisfied in the liquid reaction medium. Chemoenzymatic synthesis of (±)-4-O-(2-hydroxy-4-nitrophenyl)-1-O-trans-feruloyl-1,2,4-butanetriol (4NTC–linker–Fe, 12). Enzymatic
Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases
Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212
- -modified nucleosides were obtained in good yields. In spite of the obvious progress in using the transglycosylation reaction for the synthesis of biologically important nucleosides, the idea of researching and developing an effective method for the enzymatic or chemoenzymatic synthesis of PF-1Pis has again
Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis
Beilstein J. Org. Chem. 2019, 15, 1545–1551, doi:10.3762/bjoc.15.157
- divided into two types, depending on where the cation is generated in the isoprenoid diphosphate: the “normal” prenylation in which the C-1 is attacked and the “reverse” prenylation in which the C-3 is attacked (Figure 1). It is important to study prenylation types for the chemoenzymatic synthesis of
A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
Beilstein J. Org. Chem. 2019, 15, 490–496, doi:10.3762/bjoc.15.42
- Seema V. Kanojia Sucheta Chatterjee Subrata Chattopadhyay Dibakar Goswami Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400 094, India 10.3762/bjoc.15.42 Abstract A chemoenzymatic
- synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF6], followed by a diastereoselective asymmetric dihydroxylation as the key steps for incorporating the stereogenic centers. The further
Thiol-free chemoenzymatic synthesis of β-ketosulfides
Beilstein J. Org. Chem. 2019, 15, 378–387, doi:10.3762/bjoc.15.34
- chemoenzymatic synthesis of β-ketosulfides. One-pot two-step preparation of phenacylalkylsulfides. aReaction conditions: i. α-haloketone (0.25 mmol), potassium thioacetate (1.1 equiv), alkyl halide (1.1 equiv) and K2CO3 (2.0 equiv) in 500 µL of DMSO, 5 h at room temperature; ii. 100 mg of CAL-B (Novozyme 435
Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides
Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180
- sugar donor scope, and our group has shown the potency of this enzyme as a biocatalyst for the chemoenzymatic synthesis of non-natural desulfoglycosinolates [22]. More recently, S-glycosylated peptides have been identified, and characterized. In bacteria the structures of sublancin [23], glycocin F [24
Strategies toward protecting group-free glycosylation through selective activation of the anomeric center
Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123
- ]. On the other hand, the disadvantage is the need to synthesize NDP-sugars as substrates for the GT which is typically a multistep laborious process. Another particularly interesting application of glycosyltransferases is the chemoenzymatic synthesis of nucleosides. This is an incredibly powerful tool
Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148
- studies. Keywords: biosynthesis; chemoenzymatic synthesis; enzymology; heterocycles; polyketides; Introduction Heterocycles Heterocycles are important structural elements, which are present in natural products from all classes and also in many biologically active synthetic compounds. They often
Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction
Beilstein J. Org. Chem. 2015, 11, 2245–2251, doi:10.3762/bjoc.11.243
- synthesis of these important compounds. Keywords: α,β-unsaturated esters; carboxylic acid reductase; chemoenzymatic synthesis; reduction; Wittig reaction; Introduction α,β-Unsaturated esters are versatile building blocks for organic synthesis and of significant importance for industrial applications [1][2
Synthesis of divalent ligands of β-thio- and β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase
Beilstein J. Org. Chem. 2014, 10, 3073–3086, doi:10.3762/bjoc.10.324
- terminal units and it has been demonstrated that it plays an important role in the infection. Herein, the enzyme was also tested as a tool for the chemoenzymatic synthesis of sialic acid containing glycoclusters. The transfer reaction of sialic acid was performed using a recombinant TcTS and 3
First chemoenzymatic stereodivergent synthesis of both enantiomers of promethazine and ethopropazine
Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322
Concise total synthesis of two marine natural nucleosides: trachycladines A and B
Beilstein J. Org. Chem. 2014, 10, 1681–1685, doi:10.3762/bjoc.10.176
- perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B. Keywords: marine nucleosides; natural products; total synthesis; trachycladines A and B; Vorbrüggen glycosylation; Introduction Marine
The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases
Beilstein J. Org. Chem. 2014, 10, 1657–1669, doi:10.3762/bjoc.10.173
- 2-chloro-9-(β-D-arabinofuranosyl)adenine (6) in 45 min, the formation of 2-chloro-9-(β-D-xylofuranosyl)adenine (7) proceeded very slowly attaining ca. 8% yield in 48 h. Keywords: chemoenzymatic synthesis; clofarabine; nucleoside phosphorylases; phosphopentomutase; recombinant E. coli ribokinase
- [35]: (MeOH) λmax, nm (ε, M−1cm−1) 258 (14,600). The 1H and 13C NMR spectra of the synthesized nucleoside 4a are similar to those previously described for the authentic sample [35]. The structures of purine nucleosides studied in the chemoenzymatic synthesis and in a cascade one-pot transformation of
Stereoselectively fluorinated N-heterocycles: a brief survey
Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306
- model [74][75]. The 3,3-difluoropyrrolidine moiety (e.g. 78) is found in a variety of enzyme inhibitors such as thrombin inhibitors and cathepsin inhibitors, and so this synthetic methodology (Scheme 10) is likely to have valuable future applications in medicinal chemistry. 6.6 Chemoenzymatic synthesis
- . Chemoenzymatic synthesis of fluorinated β-lactam 4b. Fluorination improves the bioavailability of 3-piperidinylindole derivatives 38–40 by reducing the basicity of the secondary amine. Acknowledgement We thank the Australian Research Council (DE120101653) for supporting XGH’s position.
Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids
Beilstein J. Org. Chem. 2013, 9, 516–525, doi:10.3762/bjoc.9.56
- liquids to exhibit excellent antimicrobial activity, raising the possibility that ionic liquids could find application as biocidal agents in the control of microorganism growth [42][43][44][45]. Herein, we report the results of our investigation on the chemoenzymatic synthesis of new chiral ionic liquids
Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica
Beilstein J. Org. Chem. 2012, 8, 1219–1226, doi:10.3762/bjoc.8.136
- enzyme. When taken into consideration with other previously published work, it appears that this enzyme has potential utility for the chemoenzymatic synthesis of GDP-Manp analogues, which are useful probes for studying enzymes that employ this sugar nucleotide as a substrate. Keywords: chemoenzymatic
- enzyme for the chemoenzymatic synthesis of modified GDP-Manp derivatives, we describe here the preparation of all four singly methylated Manp-1P analogues 9–12, as well as the 6-deoxy-Manp-1P derivative 13, and an initial evaluation of their ability to serve as a substrate for S. enterica GDP-ManPP
- synthesis; kinetics; methylation; pyrophosphorylase; sugar nucleotide; Introduction Modified sugar nucleotide analogues are valuable probes to study glycosyltransferases and other enzymes that use these activated glycosylating agents as substrates [1][2][3][4][5]. The synthesis of natural and non-natural
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