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Search for "macrocyclic" in Full Text gives 266 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

  • Darcy J. Atkinson,
  • Briar J. Naysmith,
  • Daniel P. Furkert and
  • Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

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  • macrocyclic core of teixobactin by Reddy et al.: In 2016, Reddy et al. reported their synthetic efforts towards teixobactin (17) with a solution-phase synthesis of the macrocyclic core 109 (Scheme 24) [73]. Their synthetic approach focused on the macrolactonisation of a linear precursor 110 differing from
  • -hydroxyenduracididine 98. Total synthesis of mannopeptimycin α (12) and β (13). Synthesis of protected L-allo-enduracididine 102. The solid phase synthesis of teixobactin (17). Retrosynthesis of the macrocyclic core 109 of teixobactin (17). Synthesis of macrocycle 117. Acknowledgements The authors would like to thank
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Published 07 Nov 2016

Evidence for an iterative module in chain elongation on the azalomycin polyketide synthase

  • Hui Hong,
  • Yuhui Sun,
  • Yongjun Zhou,
  • Emily Stephens,
  • Markiyan Samborskyy and
  • Peter F. Leadlay

Beilstein J. Org. Chem. 2016, 12, 2164–2172, doi:10.3762/bjoc.12.206

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  • or module of enzymes. Examples of deviation from this paradigm, in which a module catalyses either multiple extensions or none are of interest from both a mechanistic and an evolutionary viewpoint. We present evidence that in the biosynthesis of the 36-membered macrocyclic aminopolyol lactones
  • minor differences in the macrocyclic ring [50]. However in our hands azalomycins F3a (1a, minor) and F4a (1b, major) were produced. The HRMS of the marginolactone from DSM4137 was in agreement with that expected for 1b (calcd [M + H]+: 1082.6734, found 1082.6722). Targetted gene-disruption of the azl
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Published 11 Oct 2016

The direct oxidative diene cyclization and related reactions in natural product synthesis

  • Juliane Adrian,
  • Leona J. Gross and
  • Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

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  • monensin A, another well-known ionophore antibiotic, applying an oxidative cyclization approach using potassium permanganate [64]. Amphidinolide F Amphidinolide F (24) is a marine natural product isolated from the dinoflagellate Amphidinium sp. in 1991 [65]. The macrocyclic core of these highly cytotoxic
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Published 30 Sep 2016

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

  • Mikhail Yu. Ievlev,
  • Oleg V. Ershov,
  • Mikhail Yu. Belikov,
  • Angelina G. Milovidova,
  • Viktor A. Tafeenko and
  • Oleg E. Nasakin

Beilstein J. Org. Chem. 2016, 12, 2093–2098, doi:10.3762/bjoc.12.198

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  • influenza caused by influenza A and B viruses contain a 3,4-dihydro-2H-pyran fragment [5]. Moreover, dihydropyrans have been proven to be particularly useful in the preparation of cyclic components of macrocyclic antibiotics [6][7] and as precursors in the synthesis of C-glycosides [8]. Modern and
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Published 27 Sep 2016

Rearrangements of organic peroxides and related processes

  • Ivan A. Yaremenko,
  • Vera A. Vil’,
  • Dmitry V. Demchuk and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

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Published 03 Aug 2016

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

  • Franziska Hemmerling and
  • Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

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  • the respective heterocycles. We will not cover medium-sized and macrocyclic lactones and lactams, but concentrate on small heterocycles with ring sizes between 3 and 6 atoms (for a review about macrolactones see reference [12]). Review 1 Oxygen-containing heterocycles Oxygen-containing heterocycles
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Published 20 Jul 2016

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

  • Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

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  • irradiation. Thus, the development of novel MCR based on phosphorous reagents would allow the synthesis of macrocyclic and medium or large-sized heterocyclic systems, substances which are currently underrepresented in the literature. Further, the design of new biocompatible scaffolds such as β-lactams and
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Published 21 Jun 2016

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

  • Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

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  • identified [87][90]. The most well-studied member of the family is microcin J25 (Figure 7C) from E. coli AY25. Initial structural characterisation incorrectly identified microcin J25 as a conventional head-to-tail macrocyclic peptide [91], which was later revised to the lassoed structure by multiple groups
  • peptides for each of these molecules. The sequence highlighted in blue in PatE corresponds to the core peptide for patellamide C, another macrocyclic RiPP that contains thiazoles and oxazolines. Formation of thiazoles and oxazoles in RiPPs. A) Biosynthesis of microcin B17. B) Mechanistic models for the
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Published 20 Jun 2016

Towards the total synthesis of keramaphidin B

  • Pavol Jakubec,
  • Alistair J. M. Farley and
  • Darren J. Dixon

Beilstein J. Org. Chem. 2016, 12, 1096–1100, doi:10.3762/bjoc.12.104

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  • intermolecular Diels–Alder reaction and a double late stage RCM reaction to close the two macrocyclic rings; albeit the last stage afforded 1 in 1% yield after separation of various oligomeric byproducts [4]. Our group has had a long-standing research program dedicated towards the total syntheses of the
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Published 30 May 2016

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

  • Bin Yu,
  • Hui Xing,
  • De-Quan Yu and
  • Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

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  • . Substituents attached to the isatins and ketones had little effect on the yields and enantioselectivity, regardless of their electronic properties and positions. Amino alcohol catalysts In 2014, Evano and co-workers reported a concise synthesis of the macrocyclic core of TMC-95A using the asymmetrc aldol
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Published 18 May 2016

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

  • Antonio Dávila-Céspedes,
  • Peter Hufendiek,
  • Max Crüsemann,
  • Till F. Schäberle and
  • Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

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  • . Only recently it was recognized that members of this genus have a great potential as producers of metabolites with relevant biological activities. One striking example is the 2015 described nannocystin A (10, Figure 6), a macrocyclic compound of NRPS-PKS origin with strong antiproliferative properties
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Published 13 May 2016

Creating molecular macrocycles for anion recognition

  • Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

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  • triazolophane’s rigidity and that preorganization may be crucial for the large binding affinity. To test this idea, we examined the macrocyclic effect using an oligomer (Figure 8a) that folds up around chloride [17]. The affinity decreased by four orders of magnitude to ≈100 M−1, perfectly consistent with
  • ) Pyridyl triazolophane and (b) its high-fidelity sandwich around iodide (crystal). Adapted with permission from [20], copyright 2010 Royal Society of Chemistry. Testing the (a) macrocyclic effect, and (b) effect of rigidity against (c) the parent triazolophane. (a) Representations of the four equilibria
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Published 31 Mar 2016

Self and directed assembly: people and molecules

  • Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

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  • be very memorable – one such moment was being confronted by Shinkai Sensei with a bottle of champagne to celebrate that our chiral discriminating system had just been accepted for publication in Nature [33] (Figure 5b). At the 20th International Symposium on Macrocyclic Chemistry [34] in 1995, it was
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Published 01 Mar 2016

Natural products from microbes associated with insects

  • Christine Beemelmanns,
  • Huijuan Guo,
  • Maja Rischer and
  • Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

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  • macrocyclic 26-membered lactam precursor. Although compound 24 lacks any significant antimicrobial and anticancer activity, it was shown to act as a Na+/K+ ATPase inhibitor. Subsequent studies by the same group lead to the isolation of phenylpyridines (e.g., coprismycin A (25)), dipyridines (e.g., collismycin
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Published 19 Feb 2016

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

  • Sophie Letort,
  • Sébastien Balieu,
  • William Erb,
  • Géraldine Gouhier and
  • François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

Graphical Abstract
  • detect and to degrade organophosphate nerve agents [27]. In this respect, cyclodextrins (CDs) are interesting scaffolds because of their macrocyclic structure able to bind more or less selectively some organic substrates via non covalent interactions [28][29][30]. Due to their affinity for
  • to these characterization methods, molecular modelling analysis can afford further clues to select the suitable CD derivative for one specific pesticide. This could also support the rational design of new macrocyclic compounds able to strongly interact with organophosphates. The structure of the
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Published 05 Feb 2016

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

  • Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

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  • macrocycle and the act of reading the polymer sequence would have to be performed sequentially rather than random access. Macrocycles make an appearance: macrocyclic bisintercalators and our early efforts to develop DNA probes As just illustrated, one of the major advantages of the molecular tweezer approach
  • observation that all synthetic bisintercalators of DNA were nonmacrocyclic. DNA bisintercalating natural products with macrocyclic peptide scaffolds (such as echinomycin) were known as early as 1957, but these bound with the macrocycle in a single groove [41]. We wondered whether a macrocyclic bisintercalator
  • , supramolecular catenane [42][43]. Carol Lamberson synthesized macrocyclic diacridine 23 with spermine and diamide linker chains long enough to allow binding according to the nearest neighbor exclusion principle (e.g., a complex such as 22). All the data collected showed that this “topologically constrained
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Published 25 Jan 2016

Genicunolide A, B and C: three new triterpenoids from Euphorbia geniculata

  • Alia Farozi,
  • Javid A. Banday and
  • Shakeel A. Shah

Beilstein J. Org. Chem. 2015, 11, 2707–2712, doi:10.3762/bjoc.11.291

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  • parasites, and warts [3] and as a purgative [4][5][6]. Several macrocyclic diterpenoids with antibacterial, anticancer, anti-multidrug-resistant, antifeedant, anti-HIV and analgesic activity have been isolated from different Euphorbia species. They include jatrophane, ingol and myrsinane diterpenoids [7][8
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Published 23 Dec 2015

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

  • Aurica Farcas,
  • Giulia Tregnago,
  • Ana-Maria Resmerita,
  • Pierre-Henri Aubert and
  • Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

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  • conjugated polymers [16][17][18][19][20][26][27][28][29][30][31][32][33][34][35][36][37][38]. The first step in the preparation of conjugated polyrotaxanes is the threading of macrocyclic compounds (hosts) onto linear chains (guests), when a thermodynamically unstable inclusion complex (IC) is obtained. A
  • wide variety of host molecules have the ability to encapsulate the π-conjugated backbones into their cavities based on intermolecular interactions, and thus leading to ICs. Cyclodextrins (CDs) are by far the most intensively investigated macrocyclic molecules in the synthesis of such supramolecular
  • was also synthesized by coupling 1 with 2 under similar reaction conditions (Scheme 1). TM-βCD and TM-γCD macrocyclic molecules were prepared according to previously reported procedures [47]. 1·TM-βCD and 1·TM-γCD were synthesized in water by using a 2:1 molar ratio of macrocycles and monomer 1. The
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Published 21 Dec 2015

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

  • Mino R. Caira,
  • Susan A. Bourne,
  • Halima Samsodien and
  • Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

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  • –27.6° for DIMEB pentadecahydrate (CSD refcode BOYFOK04), confirming that complexation between 2ME and DIMEB does not cause untoward host distortion, but is instead associated with a more symmetrical macrocyclic shape. On the the primary side of the DIMEB molecule, three of the torsion angles O5–C5–C6
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Published 16 Dec 2015

Smart molecules for imaging, sensing and health (SMITH)

  • Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

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  • author as director of the Notre Dame Integrated Imaging Facility. Chronological progression of Smith group research projects. Molecular transporters promote translocation of ions or hydrophilic biomolecules across a synthetic or biological membrane. Macrocyclic receptor that binds solvent separated ion
  • -pairs. Trapping a macrocyclic receptor containing a reactive ion-pair produces an interlocked [2]rotaxane. (top) Basis of Synthavidin technology. A fluorescent squaraine dye that is flanked by PEG chains can rapidly thread a tetralactam macrocycle in water to produce a highly stable complex. (bottom
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Published 10 Dec 2015

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

  • Tatjana Huber,
  • Lara Weisheit and
  • Thomas Magauer

Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273

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  • cyclononene ring could be realized in quantitative yield, the low-yielding formation of the macrocyclic thioether reduced the overall efficiency of the presented synthetic route. Based on a similar strategy and using the corresponding Z-isomer of cyclization precursor 39, Oishi and co-workers reported a total
  • synthesize a variety of natural products containing this macrocyclic structural motif. Based on chiral enone 80 and its enantiomer, ent-80, coraxeniolide A (10) and β-caryophyllene (22) were synthesized in five and four further steps, respectively. The synthesis of 10 continued with a trityl perchlorate
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Published 10 Dec 2015

Diversity-oriented synthesis of analogues of the novel macrocyclic peptide FR-225497 through late stage functionalization

  • Jyotiprasad Mukherjee,
  • Suman Sil and
  • Shital Kumar Chattopadhyay

Beilstein J. Org. Chem. 2015, 11, 2487–2492, doi:10.3762/bjoc.11.270

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  • which involves a late-stage functionalization of a macrocyclic scaffold through cross metathesis in an attempt to create diversity. The utility of this protocol is demonstrated through the preparation of three structural analogues of the important naturally occurring histone deacetylase inhibitor FR
  • [8], macrocyclic compounds are currently expanding the medicinal chemistry space [9][10]. Macrocyclic natural products [11] with significant levels of biological activity, and their analogues [12] are therefore receiving attention as targets for diversity-oriented synthesis. A class of cyclic tetra
  • [16][17] on a macrocyclic template would constitute a direct approach for grafting the pendant alkyl chain of 1, as demonstrated retrosynthetically in Figure 2. Our initial focus was on the preparation of analogues of the macrocyclic compound 4 through variation of the end groups as it has been shown
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Published 08 Dec 2015

Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex

  • Chompoonut Rungnim,
  • Sarunya Phunpee,
  • Manaschai Kunaseth,
  • Supawadee Namuangruk,
  • Kanin Rungsardthong,
  • Thanyada Rungrotmongkol and
  • Uracha Ruktanonchai

Beilstein J. Org. Chem. 2015, 11, 2306–2317, doi:10.3762/bjoc.11.251

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  • addition [2][3][4][5][6][7][8] and surfactant addition [9]. Complexation is one of the most utilized methods for enhancing the solubility of poorly soluble drugs. Cyclodextrins (CDs) are well-known macrocyclic oligosaccharides that are produced by enzymatic degradation of starch. CDs consist of 6, 7 and 8
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Published 25 Nov 2015

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

  • Jing Lin,
  • Tao Kong,
  • Lin Ye,
  • Ai-ying Zhang and
  • Zeng-guo Feng

Beilstein J. Org. Chem. 2015, 11, 2267–2277, doi:10.3762/bjoc.11.247

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  • -chain-stranded; pentablock copolymer; poly(pseudorotaxane); polyrotaxane; single-chain-stranded; Introduction Cyclodextrins (CDs) are a series of macrocyclic molecules composed of 6, 7, or 8 (α-, β-, and γ-CD, respectively) glucopyranose units. Their hydrophilic surface and hydrophobic inner cavity
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Published 23 Nov 2015

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

  • Kevin Lafaye,
  • Cyril Bosset,
  • Lionel Nicolas,
  • Amandine Guérinot and
  • Janine Cossy

Beilstein J. Org. Chem. 2015, 11, 2223–2241, doi:10.3762/bjoc.11.241

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  • synthesis of the tris-pyrrole macrocyclic pigment nonylprodigiosin [52]. A preliminary protonation of the tris-pyrrole followed by a RCM applied to 37 in the presence of the ruthenium catalyst 36 gave the macrocycle 38, which was then transformed into the saturated derivative 39 using the Wilkinson’s
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Published 18 Nov 2015
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