scholarly journals Biosynthesis of an Anti-Addiction Agent from the Iboga Plant

2019 ◽  
Author(s):  
Scott C. Farrow ◽  
Mohamed O. Kamileen ◽  
Lorenzo Caputi ◽  
Kate Bussey ◽  
Julia E. A. Mundy ◽  
...  
Keyword(s):  
Synthetic Biology ◽  
Natural Product ◽  
Opioid Addiction ◽  
Diels Alder ◽  
The Other ◽  
Biosynthetic Enzymes ◽  
Product Class ◽  
Class Discovery ◽  
Broad Scale ◽  
Effective Treatments

Abstract(−)-Ibogaine and (−)-voacangine are plant derived psychoactives that show promise as effective treatments for opioid addiction. However, these compounds are produced by hard to source plants making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (−)-voacangine, and de-esterified voacangine, which is converted to (−)-ibogaine by heating. This discovery will enable production of these compounds by synthetic biology methods. Notably, (−)-ibogaine and (−)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Discovery of these biosynthetic enzymes therefore demonstrates how nature generates both enantiomeric series of this medically important alkaloid scaffold using closely related enzymes, including those that catalyze enantioselective formal Diels-Alder reactions.One Sentence SummaryBiosynthesis of iboga alkaloids with anti-addiction promise reveals enantioselectivity of enzymatic Diels-Alder reactions.

Polar Diels-Alder Reactions Under Microwave Irradiation Employing Different Heterocyclic Compounds as Electrophiles

2019 ◽  
Vol 16 (6) ◽  
pp. 527-543 ◽  
Author(s):  
Pedro M.E. Mancini ◽  
Carla M. Ormachea ◽  
María N. Kneeteman
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Ionic Conduction ◽  
Theoretical Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
The Other ◽  
Conventional Heating ◽  
Protic Ionic Liquids ◽  
Solvent Free Conditions

During the last twenty years, our research group has been working with aromatic nitrosubstituted compounds acting as electrophiles in Polar Diels-Alder (P-DA) reactions with different dienes of diverse nucleophilicity. In this type of reaction, after the cycloaddition reaction, the nitrated compounds obtained as the [4+2] cycloadducts suffer cis-extrusion with the loss of nitrous acid and a subsequent aromatization. In this form, the reaction results are irreversible. On the other hand, the microwave-assisted controlled heating become a powerful tool in organic synthesis as it makes the reaction mixture undergo heating by a combination of thermal effects, dipolar polarization and ionic conduction. As the Diels-Alder (D-A) reaction is one of the most important process in organic synthesis, the microwave (MW) irradiation was applied instead of conventional heating, and this resulted in better yields and shorter reaction times. Several substituted heterocyclic compounds were used as electrophiles and different dienes as nucleophiles. Two experimental situations are involved: one in the presence of Protic Ionic Liquids (PILs) as solvent and the other under solvent-free conditions. The analysis is based on experimental data and theoretical calculations.

scholarly journals Commentary to “Practicing Dialectics of Technoscience During the Anthropocene” by Hub Zwart

2021 ◽  
Author(s):  
Hans-Jörg Rheinberger
Keyword(s):  
Synthetic Biology ◽  
Philosophy Of Science ◽  
The Other ◽  
Scientific Development ◽  
Current State

AbstractHub Zwart’s article is about the idea—and the practice—of an embedded philosophy of science, that is, a philosophy participating in and at the same time reflecting about the current state of the sciences facing the Anthropocene, to which I am very sympathetic. There are, however, two caveats. The first is that participation is always in danger to end up in a more or less uncritical eulogy, in the present case of synthetic biology. The second is that I have doubts about packing the historical path of scientific development into the Procrustes bed of Hegelian dialectics. This usually leads to one or the other form of teleology.

The untapped potential of plant sesterterpenoids: chemistry, biological activities and biosynthesis

2021 ◽  
Author(s):  
Kai Guo ◽  
Yan Liu ◽  
Sheng-Hong Li
Keyword(s):  
Natural Product ◽  
Biological Activities ◽  
Product Class

An overall coverage of plant sesterterpenoids including the distribution, chemistry, biological activities, biosynthesis and evolution is provided, highlighting the untapped potential of this enigmatic but promising natural product class in plants.

scholarly journals Bispericyclic Diels–Alder Dimerization of ortho‐Quinols in Natural Product (Bio)Synthesis – Bioinspired Chemical 6‐Step Synthesis of (+)‐Maytenone

2021 ◽  
Author(s):  
Philippe A. Peixoto ◽  
Mourad El Assal ◽  
Isabelle Chataigner ◽  
Frédéric Castet ◽  
Anaëlle Cornu ◽  
...  
Keyword(s):  
Natural Product ◽  
Diels Alder ◽  
Bio Synthesis

Evolution of Natural Product Scaffolds by Acyl- and Arylnitroso Hetero-Diels−Alder Reactions: New Chemistry on Piperine

2008 ◽  
Vol 73 (12) ◽  
pp. 4559-4567 ◽  
Author(s):  
Viktor Krchňák ◽  
Katherine R. Waring ◽  
Bruce C. Noll ◽  
Ute Moellmann ◽  
Hans-Martin Dahse ◽  
...  
Keyword(s):  
Natural Product ◽  
Diels Alder

Discovery of Arabidopsis UGT73C1 as a steviol-catalyzing UDP-glycosyltransferase with chemical probes

2018 ◽  
Vol 54 (52) ◽  
pp. 7179-7182 ◽  
Author(s):  
Yiqing Zhou ◽  
Weichao Li ◽  
Wenjing You ◽  
Zhengao Di ◽  
Mingli Wang ◽  
...  
Keyword(s):  
Synthetic Biology ◽  
Natural Product ◽  
Chemical Probes

A strategy for rapidly mining biological parts from plants for synthetic biology utilizing natural product-derived chemical probes has been reported.

Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3140-3152
Author(s):  
Kamal Kumar ◽  
Mohammad Rehan ◽  
Jana Flegel ◽  
Franziska Heitkamp ◽  
Jorgelina L. Pergomet ◽  
...  
Keyword(s):  
Transition Metal ◽  
Small Molecules ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Transition Metal Complexes ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hedgehog Pathway ◽  
Diels Alder Reaction ◽  
Efficient Access

An enantioselective hetero-Diels–Alder reaction of alkylidene­ oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spiroox­indole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.

scholarly journals The Total Synthesis of (–)-Scabrolide a

2020 ◽  
Author(s):  
Nicholas Hafeman ◽  
Steven A. Loskot ◽  
Chris Reimann ◽  
Beau P. Pritchett ◽  
Scott C. Virgil ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone-olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and to complete the total synthesis.

A High-Yield Streptomyces Transcription-Translation Toolkit for Synthetic Biology and Natural Product Applications

10.3791/63012 ◽  
2021 ◽  
Author(s):  
Ming Toh ◽  
Kameshwari Chengan ◽  
Tanith Hanson ◽  
Paul S. Freemont ◽  
Simon J. Moore
Keyword(s):  
Synthetic Biology ◽  
Natural Product ◽  
High Yield
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