Total synthesis and isolation of citrinalin and cyclopiamine congeners.

Abstract:

:Many natural products that contain basic nitrogen atoms--for example alkaloids like morphine and quinine-have the potential to treat a broad range of human diseases. However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of nitrogen atoms and their susceptibility to oxidation. Obtaining such compounds by chemical synthesis can be further complicated by the presence of multiple nitrogen atoms, but it can be done by the selective introduction and removal of functional groups that mitigate basicity. Here we use such a strategy to complete the chemical syntheses of citrinalin B and cyclopiamine B. The chemical connections that have been realized as a result of these syntheses, in addition to the isolation of both 17-hydroxycitrinalin B and citrinalin C (which contains a bicyclo[2.2.2]diazaoctane structural unit) through carbon-13 feeding studies, support the existence of a common bicyclo[2.2.2]diazaoctane-containing biogenetic precursor to these compounds, as has been proposed previously.

journal_name

Nature

journal_title

Nature

authors

Mercado-Marin EV,Garcia-Reynaga P,Romminger S,Pimenta EF,Romney DK,Lodewyk MW,Williams DE,Andersen RJ,Miller SJ,Tantillo DJ,Berlinck RGS,Sarpong R

doi

10.1038/nature13273

subject

Has Abstract

pub_date

2014-05-15 00:00:00

pages

318-324

issue

7500

eissn

0028-0836

issn

1476-4687

journal_volume

509

pub_type

杂志文章

相关文献

NATURE文献大全
  • HLA-DMA and -DMB genes are both required for MHC class II/peptide complex formation in antigen-presenting cells.

    abstract::Major histocompatibility complex (MHC) class II molecules are highly polymorphic cell-surface glycoproteins that present antigenic peptides to CD4+ T lymphocytes. The normal assembly of class II molecules with cognate peptides for antigen presentation requires an accessory function provided by a gene mapping to the cl...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/368554a0

    authors: Fling SP,Arp B,Pious D

    更新日期:1994-04-07 00:00:00

  • The stepwise assembly of the neonatal virome is modulated by breastfeeding.

    abstract::The gut of healthy human neonates is usually devoid of viruses at birth, but quickly becomes colonized, which-in some cases-leads to gastrointestinal disorders1-4. Here we show that the assembly of the viral community in neonates takes place in distinct steps. Fluorescent staining of virus-like particles purified from...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/s41586-020-2192-1

    authors: Liang G,Zhao C,Zhang H,Mattei L,Sherrill-Mix S,Bittinger K,Kessler LR,Wu GD,Baldassano RN,DeRusso P,Ford E,Elovitz MA,Kelly MS,Patel MZ,Mazhani T,Gerber JS,Kelly A,Zemel BS,Bushman FD

    更新日期:2020-05-01 00:00:00

  • RNA-catalysed RNA polymerization using nucleoside triphosphates.

    abstract::The hypothesis that certain RNA molecules may be able to catalyse RNA replication is central to current theories of the early evolution of life. In support of this idea, we describe here an RNA that synthesizes RNA using the same reaction as that employed by protein enzymes that catalyse RNA polymerization. In the pre...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/382373a0

    authors: Ekland EH,Bartel DP

    更新日期:1996-07-25 00:00:00

  • Handover mechanism of the growing pilus by the bacterial outer-membrane usher FimD.

    abstract::Pathogenic bacteria such as Escherichia coli assemble surface structures termed pili, or fimbriae, to mediate binding to host-cell receptors1. Type 1 pili are assembled via the conserved chaperone-usher pathway2-5. The outer-membrane usher FimD recruits pilus subunits bound by the chaperone FimC via the periplasmic N-...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/s41586-018-0587-z

    authors: Du M,Yuan Z,Yu H,Henderson N,Sarowar S,Zhao G,Werneburg GT,Thanassi DG,Li H

    更新日期:2018-10-01 00:00:00

  • Effective combinatorial immunotherapy for castration-resistant prostate cancer.

    abstract::A significant fraction of patients with advanced prostate cancer treated with androgen deprivation therapy experience relapse with relentless progression to lethal metastatic castration-resistant prostate cancer (mCRPC). Immune checkpoint blockade using antibodies against cytotoxic-T-lymphocyte-associated protein 4 (C...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature21676

    authors: Lu X,Horner JW,Paul E,Shang X,Troncoso P,Deng P,Jiang S,Chang Q,Spring DJ,Sharma P,Zebala JA,Maeda DY,Wang YA,DePinho RA

    更新日期:2017-03-30 00:00:00

  • Excretion, isolation and structure of a new phenolic constituent of female urine.

    abstract::The regular occurrence of a peak due to an unidentified substance (X) in the gas chromatographic traces obtained from phenolic extracts of urine from human pregnant and non-pregnant females has been reported. The biphasic excretion of X with maxima in the luteal phase of the ovulatory cycle and relatively high levels ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/287738a0

    authors: Stitch SR,Toumba JK,Groen MB,Funke CW,Leemhuis J,Vink J,Woods GF

    更新日期:1980-10-23 00:00:00

  • Fusion of isolated plant protoplasts.

    abstract::A first step towards somatic hybridization in plants has been achieved. Protoplasts have been isolated and seen to fuse. ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/2251016a0

    authors: Power JB,Cummins SE,Cocking EC

    更新日期:1970-03-14 00:00:00

  • A primitive therizinosauroid dinosaur from the Early Cretaceous of Utah.

    abstract::Therizinosauroids are an enigmatic group of dinosaurs known mostly from the Cretaceous period of Asia, whose derived members are characterized by elongate necks, laterally expanded pelves, small, leaf-shaped teeth, edentulous rostra and mandibular symphyses that probably bore keratinized beaks. Although more than a do...

    journal_title:Nature

    pub_type: 历史文章,杂志文章

    doi:10.1038/nature03468

    authors: Kirkland JI,Zanno LE,Sampson SD,Clark JM,DeBlieux DD

    更新日期:2005-05-05 00:00:00

  • Sensitivity for vertical retinal image differences.

    abstract::The detection of horizontal disparities between the right and left retinal images is accepted as an important component in the visual perception of depth. It has occasionally been pointed out that a disparity will also occur in the vertical when a target is nearer to one eye than the other and could be used as a secon...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/307632a0

    authors: Westheimer G

    更新日期:1984-02-16 00:00:00

  • Major histocompatibility complex class I molecules internalized via coated pits in T lymphocytes.

    abstract::Endocytosis of the major histocompatibility complex (MHC)-encoded class I and class II molecules has been the subject of recent investigations. Class I molecules, which are key elements in T cell-mediated cytotoxicity, are differentially endocytosed by different cell types. Fibroblasts internalize their class I molecu...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/328724a0

    authors: Machy P,Truneh A,Gennaro D,Hoffstein S

    更新日期:1987-08-20 00:00:00

  • Splicing factor Sub2p is required for nuclear mRNA export through its interaction with Yra1p.

    abstract::The yeast nuclear protein Yra1p is an essential export factor for mRNA. Yra1p interacts directly with the mRNA transport factor Mex67p/Mtr2p, which is associated with the nuclear pore. Here, we report a genetic interaction between YRA1 and SUB2, the gene for a DEAD box helicase involved in splicing. Mutation of SUB2 a...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/35098113

    authors: Strässer K,Hurt E

    更新日期:2001-10-11 00:00:00

  • Confocal non-line-of-sight imaging based on the light-cone transform.

    abstract::How to image objects that are hidden from a camera's view is a problem of fundamental importance to many fields of research, with applications in robotic vision, defence, remote sensing, medical imaging and autonomous vehicles. Non-line-of-sight (NLOS) imaging at macroscopic scales has been demonstrated by scanning a ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature25489

    authors: O'Toole M,Lindell DB,Wetzstein G

    更新日期:2018-03-15 00:00:00

  • Immune clearance of highly pathogenic SIV infection.

    abstract::Established infections with the human and simian immunodeficiency viruses (HIV and SIV, respectively) are thought to be permanent with even the most effective immune responses and antiretroviral therapies only able to control, but not clear, these infections. Whether the residual virus that maintains these infections ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature12519

    authors: Hansen SG,Piatak M Jr,Ventura AB,Hughes CM,Gilbride RM,Ford JC,Oswald K,Shoemaker R,Li Y,Lewis MS,Gilliam AN,Xu G,Whizin N,Burwitz BJ,Planer SL,Turner JM,Legasse AW,Axthelm MK,Nelson JA,Früh K,Sacha JB,Estes JD

    更新日期:2013-10-03 00:00:00

  • A supermassive black hole in an ultra-compact dwarf galaxy.

    abstract::Ultra-compact dwarf galaxies are among the densest stellar systems in the Universe. These systems have masses of up to 2 × 10(8) solar masses, but half-light radii of just 3-50 parsecs. Dynamical mass estimates show that many such dwarfs are more massive than expected from their luminosity. It remains unclear whether ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature13762

    authors: Seth AC,van den Bosch R,Mieske S,Baumgardt H,den Brok M,Strader J,Neumayer N,Chilingarian I,Hilker M,McDermid R,Spitler L,Brodie J,Frank MJ,Walsh JL

    更新日期:2014-09-18 00:00:00

  • RecA acts in trans to allow replication of damaged DNA by DNA polymerase V.

    abstract::The DNA polymerase V (pol V) and RecA proteins are essential components of a mutagenic translesion synthesis pathway in Escherichia coli designed to cope with DNA damage. Previously, it has been assumed that RecA binds to the DNA template strand being copied. Here we show, however, that pol-V-catalysed translesion syn...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature05042

    authors: Schlacher K,Cox MM,Woodgate R,Goodman MF

    更新日期:2006-08-24 00:00:00

  • Milestone meetings.

    abstract:: ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/d41586-018-07781-4

    authors: Gewin V

    更新日期:2018-12-01 00:00:00

  • The catalytic mechanism for aerobic formation of methane by bacteria.

    abstract::Methane is a potent greenhouse gas that is produced in significant quantities by aerobic marine organisms. These bacteria apparently catalyse the formation of methane through the cleavage of the highly unreactive carbon-phosphorus bond in methyl phosphonate (MPn), but the biological or terrestrial source of this compo...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature12061

    authors: Kamat SS,Williams HJ,Dangott LJ,Chakrabarti M,Raushel FM

    更新日期:2013-05-02 00:00:00

  • Long-term culture of murine erythropoietic progenitor cells in the absence of an adherent layer.

    abstract::Replication of multipotential stem cells in long-term murine bone marrow cell culture is known to depend on the development of an adherent stromal cell layer. In these conditions, restricted haematopoietic progenitor cells have also been generated for up to several months1-3. However, maturation is observed only in th...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/305625a0

    authors: Wendling F,Shreeve MM,McLeod DL,Axelrad AA

    更新日期:1983-10-13 00:00:00

  • Crystal structure of nerve growth factor in complex with the ligand-binding domain of the TrkA receptor.

    abstract::Nerve growth factor (NGF) is involved in a variety of processes involving signalling, such as cell differentiation and survival, growth cessation and apoptosis of neurons. These events are mediated by NGF as a result of binding to its two cell-surface receptors, TrkA and p75. TrkA is a receptor with tyrosine kinase ac...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/43705

    authors: Wiesmann C,Ultsch MH,Bass SH,de Vos AM

    更新日期:1999-09-09 00:00:00

  • Programmed population control by cell-cell communication and regulated killing.

    abstract::De novo engineering of gene circuits inside cells is extremely difficult, and efforts to realize predictable and robust performance must deal with noise in gene expression and variation in phenotypes between cells. Here we demonstrate that by coupling gene expression to cell survival and death using cell-cell communic...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature02491

    authors: You L,Cox RS 3rd,Weiss R,Arnold FH

    更新日期:2004-04-22 00:00:00

  • Mechanism of differential control of NMDA receptor activity by NR2 subunits.

    abstract::N-methyl-d-aspartate (NMDA) receptors (NMDARs) are a major class of excitatory neurotransmitter receptors in the central nervous system. They form glutamate-gated ion channels that are highly permeable to calcium and mediate activity-dependent synaptic plasticity. NMDAR dysfunction is implicated in multiple brain diso...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature07993

    authors: Gielen M,Siegler Retchless B,Mony L,Johnson JW,Paoletti P

    更新日期:2009-06-04 00:00:00

  • The histone H3.3 chaperone HIRA is essential for chromatin assembly in the male pronucleus.

    abstract::In sexually reproducing animals, a crucial step in zygote formation is the decondensation of the fertilizing sperm nucleus into a DNA replication-competent male pronucleus. Genome-wide nucleosome assembly on paternal DNA implies the replacement of sperm chromosomal proteins, such as protamines, by maternally provided ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature04059

    authors: Loppin B,Bonnefoy E,Anselme C,Laurençon A,Karr TL,Couble P

    更新日期:2005-10-27 00:00:00

  • Why the Bank of England should put a female scientist on its next £50 note.

    abstract:: ...

    journal_title:Nature

    pub_type: 新闻

    doi:10.1038/d41586-018-07324-x

    authors:

    更新日期:2018-11-01 00:00:00

  • A salt-water reservoir as the source of a compositionally stratified plume on Enceladus.

    abstract::The discovery of a plume of water vapour and ice particles emerging from warm fractures ('tiger stripes') in Saturn's small, icy moon Enceladus raised the question of whether the plume emerges from a subsurface liquid source or from the decomposition of ice. Previous compositional analyses of particles injected by the...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature10175

    authors: Postberg F,Schmidt J,Hillier J,Kempf S,Srama R

    更新日期:2011-06-22 00:00:00

  • Continuing Colorado plateau uplift by delamination-style convective lithospheric downwelling.

    abstract::The Colorado plateau is a large, tectonically intact, physiographic province in the southwestern North American Cordillera that stands at ∼1,800-2,000 m elevation and has long been thought to be in isostatic equilibrium. The origin of these high elevations is unclear because unlike the surrounding provinces, which hav...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature10001

    authors: Levander A,Schmandt B,Miller MS,Liu K,Karlstrom KE,Crow RS,Lee CT,Humphreys ED

    更新日期:2011-04-28 00:00:00

  • Heterochromatin drives compartmentalization of inverted and conventional nuclei.

    abstract::The nucleus of mammalian cells displays a distinct spatial segregation of active euchromatic and inactive heterochromatic regions of the genome1,2. In conventional nuclei, microscopy shows that euchromatin is localized in the nuclear interior and heterochromatin at the nuclear periphery1,2. Genome-wide chromosome conf...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/s41586-019-1275-3

    authors: Falk M,Feodorova Y,Naumova N,Imakaev M,Lajoie BR,Leonhardt H,Joffe B,Dekker J,Fudenberg G,Solovei I,Mirny LA

    更新日期:2019-06-01 00:00:00

  • Disease resistance results from foreign phytoalexin expression in a novel plant.

    abstract::Although phytoalexins have long been inferred to be important in the defence of plants against fungal infection, there are few reports showing that they provide resistance to infection. Several plants, including grapevine, synthesize the stilbene-type phytoalexin resveratrol when attacked by pathogens. Stilbenes with ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/361153a0

    authors: Hain R,Reif HJ,Krause E,Langebartels R,Kindl H,Vornam B,Wiese W,Schmelzer E,Schreier PH,Stöcker RH

    更新日期:1993-01-14 00:00:00

  • Survival variability and population density in fish populations.

    abstract::To understand the processes that regulate the abundance and persistence of wild populations is a fundamental goal of ecology and a prerequisite for the management of living resources. Variable abundance data, however, make the demonstration of regulation processes challenging. A previously overlooked aspect in underst...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature06605

    authors: Minto C,Myers RA,Blanchard W

    更新日期:2008-03-20 00:00:00

  • Structure of the V. cholerae Na+-pumping NADH:quinone oxidoreductase.

    abstract::NADH oxidation in the respiratory chain is coupled to ion translocation across the membrane to build up an electrochemical gradient. The sodium-translocating NADH:quinone oxidoreductase (Na(+)-NQR), a membrane protein complex widespread among pathogenic bacteria, consists of six subunits, NqrA, B, C, D, E and F. To ou...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature14003

    authors: Steuber J,Vohl G,Casutt MS,Vorburger T,Diederichs K,Fritz G

    更新日期:2014-12-04 00:00:00

  • A universal model for mobility and migration patterns.

    abstract::Introduced in its contemporary form in 1946 (ref. 1), but with roots that go back to the eighteenth century, the gravity law is the prevailing framework with which to predict population movement, cargo shipping volume and inter-city phone calls, as well as bilateral trade flows between nations. Despite its widespread ...

    journal_title:Nature

    pub_type: 杂志文章

    doi:10.1038/nature10856

    authors: Simini F,González MC,Maritan A,Barabási AL

    更新日期:2012-02-26 00:00:00