Search Results - "GROSSMAN, Robert B"
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Research Progress of Polycyclic Polyprenylated Acylphloroglucinols
Published in Chemical reviews (11-04-2018)“…Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide…”
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Structural Revision of Garcinielliptin Oxide and Garcinielliptone E
Published in Journal of natural products (Washington, D.C.) (26-06-2020)“…Previously, Lin et al. reported the isolation and structural determination of two triterpenoids, garcinielliptin oxide (GO) and garcinielliptone E (GE). Their…”
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3
Evidence for Modulation of Oxygen Rebound Rate in Control of Outcome by Iron(II)- and 2‑Oxoglutarate-Dependent Oxygenases
Published in Journal of the American Chemical Society (25-09-2019)“…Iron(II)- and 2-oxoglutarate-dependent (Fe/2OG) oxygenases generate iron(IV)-oxo (ferryl) intermediates that can abstract hydrogen from aliphatic carbons…”
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Installation of the Ether Bridge of Lolines by the Iron- and 2‑Oxoglutarate-Dependent Oxygenase, LolO: Regio- and Stereochemistry of Sequential Hydroxylation and Oxacyclization Reactions
Published in Biochemistry (Easton) (10-04-2018)“…The core of the loline family of insecticidal alkaloids is the bicyclic pyrrolizidine unit with an additional strained ether bridge between carbons 2 and 7…”
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Enzymes from fungal and plant origin required for chemical diversification of insecticidal loline alkaloids in grass-Epichloë symbiota
Published in PloS one (22-12-2014)“…The lolines are a class of bioprotective alkaloids that are produced by Epichloë species, fungal endophytes of grasses. These alkaloids are saturated…”
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1,2-Diamination of Alkenes via 1,3-Dipolar Cycloaddition with Azidium Ions or Azides
Published in Organic letters (20-01-2023)“…We describe two new methods for the 1,2-diamination of alkenes. First, either an azidium ion (ArNN+NAr) undergoes 1,3-dipolar cycloaddition with an alkene to…”
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Polycyclic Polyprenylated Acylphloroglucinols
Published in Chemical reviews (01-09-2006)“…Investigation of the chemical activity of plants used in herbal medicine, such as St John's Wort and hops, have revealed a class of compounds, polycyclic…”
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Revision of the Structure of Hypatulone A by NMR, Computations, and Biosynthetic Considerations
Published in Organic letters (17-01-2020)“…Recently, a paper in this journal reported the isolation and structure determination of hypatulone A. Several features of the proposed structure and…”
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Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring
Published in Journal of natural products (Washington, D.C.) (27-10-2023)“…Four previous papers reported the isolation and structural determination of 10 polycyclic polyprenylated acylphloroglucinols (PPAPs), uraliones F, G, K, and O,…”
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Total synthesis and structural reassignment of garcinielliptone FC, a polycyclic polyprenylated acylphloroglucinol with diverse bioactivity
Published in Chemical communications (Cambridge, England) (18-05-2023)“…Garcinielliptone FC (GFC) was assigned to be a type A polycyclic polyprenylated acylphloroglucinol (PPAP) and was found to exhibit diverse biological…”
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11
A Conformationally Restricted Gold(III) Complex Elicits Antiproliferative Activity in Cancer Cells
Published in Inorganic chemistry (14-08-2023)“…Diamine ligands are effective structural scaffolds for tuning the reactivity of transition-metal complexes for catalytic, materials, and phosphorescent…”
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Polycyclic Polyprenylated Acylphloroglucinols Bearing a Lavandulyl-Derived Substituent from Garcinia xanthochymus Fruits
Published in Journal of natural products (Washington, D.C.) (23-12-2022)“…Many type B polycyclic polyprenylated acylphloroglucinols (PPAPs) bear a lavandulyl-derived substituent, and the configurational assignment of this side chain…”
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13
A New Synthetic Approach to the Polycyclic Polyprenylated Acylphloroglucinols
Published in Organic letters (27-11-2003)“…The three-carbon α,α‘-annulation of a sterically hindered cyclic β-keto ester can be achieved by alkynylation with 3,3-diethoxypropyne, syn reduction of the…”
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14
An Unusual Ferryl Intermediate and Its Implications for the Mechanism of Oxacyclization by the Loline-Producing Iron(II)- and 2‑Oxoglutarate-Dependent Oxygenase, LolO
Published in Biochemistry (Easton) (02-07-2024)“…N-Acetylnorloline synthase (LolO) is one of several iron(II)- and 2-oxoglutarate-dependent (Fe/2OG) oxygenases that catalyze sequential reactions of different…”
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Synthesis of 6,6‐ and 7,7‐Difluoro‐1‐acetamidopyrrolizidines and Their Oxidation Catalyzed by the Nonheme Fe Oxygenase LolO
Published in Chembiochem : a European journal of chemical biology (05-07-2022)“…LolO, a 2‐oxoglutarate‐dependent nonheme Fe oxygenase, catalyzes both the hydroxylation of 1‐exo‐acetamidopyrrolizidine (AcAP), a pathway intermediate in the…”
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Structural Revision of Hyperibrin B and Hyperscabrones H and I by Biosynthetic Considerations, NMR Analysis, and Chemical Synthesis
Published in Journal of natural products (Washington, D.C.) (23-07-2021)“…Previously, Gao et al. reported the isolation and structural determination of three natural products, hyperibrin B (HB), hyperscabrone H (HH), and…”
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Loline alkaloids: Currencies of mutualism
Published in Phytochemistry (Oxford) (01-04-2007)“…Increasingly, fungal endophytes are recognized for their roles in plant protection. Several seed-borne endophytes of grasses (Poaceae) produce lolines, which…”
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Insights into the substrate specificity of plant peptide deformylase, an essential enzyme with potential for the development of novel biotechnology applications in agriculture
Published in Biochemical journal (01-08-2008)“…The crystal structure of AtPDF1B [Arabidopsis thaliana PDF (peptide deformylase) 1B; EC 3.5.1.88], a plant specific deformylase, has been determined at a…”
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Ether bridge formation in loline alkaloid biosynthesis
Published in Phytochemistry (Oxford) (01-02-2014)“…The LolO non-heme iron oxygenase is required to form the ether bridge of loline alkaloids. •Genomes were sequenced for four fungi with three different loline…”
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An unusually short inter-molecular N-H⋯N hydrogen bond in crystals of the hemi-hydro-chloride salt of 1- exo -acetamido-pyrrolizidine
Published in Acta crystallographica. Section E, Crystallographic communications (01-01-2020)“…The title compound [systematic name: (1 *, 8 )-2-acetamidoocta-hydro-pyrrol-izin-4-ium chloride- -[(1 , 8 )-hexa-hydro-1 -pyrrolizin-2-yl)acetamide (1/1)], 2(C…”
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