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Showing 1 to 11 of 11 entries
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Complete biosynthesis of the bisbenzylisoquinoline alkaloids guattegaumerine and berbamunine in yeast.

Proceedings of the National Academy of Sciences of the United States of America

Payne JT, Valentic TR, Smolke CD.
PMID: 34903659
Proc Natl Acad Sci U S A. 2021 Dec 21;118(51). doi: 10.1073/pnas.2112520118.

Benzylisoquinoline alkaloids (BIAs) are a diverse class of medicinal plant natural products. Nearly 500 dimeric bisbenzylisoquinoline alkaloids (bisBIAs), produced by the coupling of two BIA monomers, have been characterized and display a range of pharmacological properties, including anti-inflammatory, antitumor,...

Ion trap MS(n) genealogical mapping-approaches for structure elucidation of novel products of consecutive fragmentations of morphinans.

Rapid communications in mass spectrometry : RCM

Strife RJ, Robosky LC, Garrett G, Ketcha MM, Shaffer JD, Zhang N.
PMID: 10669884
Rapid Commun Mass Spectrom. 2000;14(4):250-60. doi: 10.1002/(SICI)1097-0231(20000229)14:4<250::AID-RCM865>3.0.CO;2-9.

The analysis of data within multi-generational, genealogical, electrospray ionization/MS(n) fragmentation maps is discussed in reference to the structure elucidation of morphinans, an important class of pharmacological compounds. Various general approaches to separate and understand observed processes are discussed. These...

Peripherally active dextromethorphan derivatives lower blood glucose levels by targeting pancreatic islets.

Cell chemical biology

Scholz O, Otter S, Welters A, Wörmeyer L, Dolenšek J, Klemen MS, Pohorec V, Eberhard D, Mrugala J, Hamacher A, Koch A, Sanz M, Hoffmann T, Hogeback J, Herebian D, Klöcker N, Piechot A, Mayatepek E, Meissner T, Stožer A, Lammert E.
PMID: 34118188
Cell Chem Biol. 2021 Oct 21;28(10):1474-1488.e7. doi: 10.1016/j.chembiol.2021.05.011. Epub 2021 Jun 11.

Dextromethorphan (DXM) acts as cough suppressant via its central action. Cell-protective effects of this drug have been reported in peripheral tissues, making DXM potentially useful for treatment of several common human diseases, such as type 2 diabetes mellitus (T2DM)....

Novel class of morphinans with acrylonitrile incorporated substructures as key intermediates for non-oxygen-bridged opioid ligands.

Journal of the American Chemical Society

Greiner E, Schottenberger H, Wurst K, Schmidhammer H.
PMID: 11457125
J Am Chem Soc. 2001 Apr 25;123(16):3840-1. doi: 10.1021/ja015550r.

No abstract available.

Frontiers in pharmacology

Lattanzi R, Rief S, Schmidhammer H, Negri L, Spetea M.
PMID: 30233377
Front Pharmacol. 2018 Aug 31;9:1002. doi: 10.3389/fphar.2018.01002. eCollection 2018.

Pain, particularly chronic pain, is still an unsolved medical condition. Central goals in pain control are to provide analgesia of adequate efficacy and to reduce complications associated with the currently available drugs. Opioids are the mainstay for the treatment...

DARK Classics in Chemical Neuroscience: Krokodil.

ACS chemical neuroscience

Alves EA.
PMID: 32877160
ACS Chem Neurosci. 2020 Sep 17; doi: 10.1021/acschemneuro.0c00495. Epub 2020 Sep 17.

Krokodil is the street name for a homemade mixture that has been used as a cheap substitute for heroin. The main active substance in krokodil is desomorphine, an opioid that is 10 times more potent than morphine. Krokodil use...

Programmed serial stereochemical relay and its application in the synthesis of morphinans.

Chemical science

Ho Kenny Park K, Chen R, Chen DY.
PMID: 29147530
Chem Sci. 2017 Oct 01;8(10):7031-7037. doi: 10.1039/c7sc03189k. Epub 2017 Aug 30.

Herein we report a rationally designed, serial point-to-axial and axial-to-point stereoinduction and its integration into multi-step and target-oriented organic synthesis. In this proof-of-concept study, the configurational stability of several carefully designed atropisomeric intermediates and the fidelity of their unconventional...

Peripherally active dextromethorphan derivatives lower blood glucose levels by targeting pancreatic islets.

Cell chemical biology

Scholz O, Otter S, Welters A, Wörmeyer L, Dolenšek J, Klemen MS, Pohorec V, Eberhard D, Mrugala J, Hamacher A, Koch A, Sanz M, Hoffmann T, Hogeback J, Herebian D, Klöcker N, Piechot A, Mayatepek E, Meissner T, Stožer A, Lammert E.
PMID: 34118188
Cell Chem Biol. 2021 Oct 21;28(10):1474-1488.e7. doi: 10.1016/j.chembiol.2021.05.011. Epub 2021 Jun 11.

Dextromethorphan (DXM) acts as cough suppressant via its central action. Cell-protective effects of this drug have been reported in peripheral tissues, making DXM potentially useful for treatment of several common human diseases, such as type 2 diabetes mellitus (T2DM)....

Studies toward bivalent κ opioids derived from salvinorin A: heteromethylation of the furan ring reduces affinity.

Beilstein journal of organic chemistry

Munro TA, Xu W, Ho DM, Liu-Chen LY, Cohen BM.
PMID: 24454571
Beilstein J Org Chem. 2013 Dec 20;9:2916-24. doi: 10.3762/bjoc.9.328. eCollection 2013 Dec 20.

The recent crystal structure of the κ-opioid receptor (κ-OR) revealed, unexpectedly, that the antagonist JDTic is a bivalent ligand: in addition to the orthosteric pocket occupied by morphinans, JDTic also occupies a distinct (allotopic) pocket. Mutagenesis data suggest that...

Enantioenriched Methylene-Bridged Benzazocanes Synthesis by Organocatalytic and Superacid Activations.

Angewandte Chemie (International ed. in English)

Beaud R, Michelet B, Reviriot Y, Martin-Mingot A, Rodriguez J, Bonne D, Thibaudeau S.
PMID: 31797509
Angew Chem Int Ed Engl. 2020 Jan 13;59(3):1279-1285. doi: 10.1002/anie.201912043. Epub 2019 Dec 04.

Achieving in a straightforward way the synthesis of enantioenriched elaborated three-dimensional molecules related to bioactive natural products remains a long-standing quest in organic synthesis. Enantioselective organocatalysis potentially offers a unique opportunity to solve this problem, especially when combined with...

Complete biosynthesis of the bisbenzylisoquinoline alkaloids guattegaumerine and berbamunine in yeast.

Proceedings of the National Academy of Sciences of the United States of America

Payne JT, Valentic TR, Smolke CD.
PMID: 34903659
Proc Natl Acad Sci U S A. 2021 Dec 21;118(51). doi: 10.1073/pnas.2112520118.

Benzylisoquinoline alkaloids (BIAs) are a diverse class of medicinal plant natural products. Nearly 500 dimeric bisbenzylisoquinoline alkaloids (bisBIAs), produced by the coupling of two BIA monomers, have been characterized and display a range of pharmacological properties, including anti-inflammatory, antitumor,...

Showing 1 to 11 of 11 entries