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Current Trends towards Natural Products Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (28 February 2022) | Viewed by 3680

Special Issue Editors

Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, 80126 Naples, Italy
Interests: isolation and structure elucidation of natural compounds from microorganisms and plants; synthesis and derivatization of natural products; chromatographic techniques; analytical and spectroscopic techniques
Special Issues, Collections and Topics in MDPI journals
Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, 80126 Naples, Italy
Interests: synthesis and characterization of heterocycles, mainly furans; organic photochemistry; sustainable methodologies for natural compounds or their analogues of biological interest; mechanistic aspects

Special Issue Information

Dear Colleagues,

The field of total synthesis of natural products has evolved intensely over the past 30 years owing to the efforts of strategy-based organic chemists, along with remarkable improvements in our bond-forming capabilities. In addition to the search for novel strategies, efforts are also addressed at translating laboratory-level academic success in total synthesis to the large-scale assembly of biologically important molecules, or building large collections of natural product families (or their analogues) for use as biological probes or in medicinal chemistry or to gather information on the structure–activity relationship (SAR) for a particular natural product in order to synthetize simplified derivatives. You are invited to submit research/reviews on topics from the natural product synthesis field.

Prof. Dr. Marina DellaGreca
Prof. Dr. Maria Rosaria Iesce
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • stereoselective synthesis
  • structure–activity relationship
  • sustainable methodology
  • natural product engineering tool
  • functionalization strategies

Published Papers (2 papers)

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Research

11 pages, 1367 KiB  
Article
Chemoenzymatic Synthesis of Select Intermediates and Natural Products of the Desferrioxamine E Siderophore Pathway
by Katherine M. Hoffmann, Jason S. Kingsbury, Nathan L. March, Yoojin Jang, James H. Nguyen and Miranda M. Hutt
Molecules 2022, 27(19), 6144; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27196144 - 20 Sep 2022
Cited by 2 | Viewed by 1486
Abstract
The NIS synthetase family of enzymes responsible for the biosynthesis of siderophores is increasingly associated with bacterial virulence. Proteins in this class represent outstanding potential drug targets, assuming that basic biochemical and structural characterizations can be completed. Towards this goal, we have mated [...] Read more.
The NIS synthetase family of enzymes responsible for the biosynthesis of siderophores is increasingly associated with bacterial virulence. Proteins in this class represent outstanding potential drug targets, assuming that basic biochemical and structural characterizations can be completed. Towards this goal, we have mated an improved synthesis of the non-commercial amino acid N-hydroxy-N-succinylcadaverine (HSC, 6) with an isothermal titration calorimetry (ITC) assay that profiles the iterative stages of HSC trimerization and macrocyclization by NIS synthetase DesD from Streptomyces coelicolor. HSC synthesis begins with multigram-scale Gabrielle and tert-butyl N-(benzyloxy)carbamate alkylations of 1-bromo-5-chloropentane following prior literature, but the end-game reported herein has two advantages for greater material throughput: (1) hydrogenolysis of benzyl ether and Cbz blocking groups is best accomplished with Pearlman’s catalyst at 40 psi of H2 and (2) purification of neutral (zwitterionic) HSC is effected by simple flash chromatography over silica gel in MeOH. HSC is subsequently shown to be a substrate for NIS synthetase DesD, which catalyzes three successive amide bond syntheses via adenyl monophosphate ester intermediates. We quantify and present the iterative and overall enzyme kinetic constants associated with formation of the cyclotrimeric siderophore desferrioxamine E (dfoE, 1). Full article
(This article belongs to the Special Issue Current Trends towards Natural Products Synthesis)
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9 pages, 1350 KiB  
Article
Secondary Metabolites, including a New 5,6-Dihydropyran-2-One, Produced by the Fungus Diplodia corticola. Aphicidal Activity of the Main Metabolite, Sphaeropsidin A
by Maria Michela Salvatore, Ilaria Di Lelio, Marina DellaGreca, Rosario Nicoletti, Francesco Salvatore, Elia Russo, Gennaro Volpe, Andrea Becchimanzi, Alla Eddine Mahamedi, Akila Berraf-Tebbal and Anna Andolfi
Molecules 2022, 27(7), 2327; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27072327 - 04 Apr 2022
Cited by 5 | Viewed by 1697
Abstract
An undescribed 5,6-dihydropyran-2-one, namely diplopyrone C, was isolated and characterized from the cultures of an isolate of the fungus Diplodia corticola recovered from Quercus suber in Algeria. The structure and relative stereostructure of (5S,6S,7Z,9S,10S)-5-hydroxy-6-(2-(3-methyloxiran-2-yl)vinyl)-5,6-dihydro-2H-pyran-2-one were [...] Read more.
An undescribed 5,6-dihydropyran-2-one, namely diplopyrone C, was isolated and characterized from the cultures of an isolate of the fungus Diplodia corticola recovered from Quercus suber in Algeria. The structure and relative stereostructure of (5S,6S,7Z,9S,10S)-5-hydroxy-6-(2-(3-methyloxiran-2-yl)vinyl)-5,6-dihydro-2H-pyran-2-one were assigned essentially based on NMR and MS data. Furthermore, ten known compounds were isolated and identified in the same cultures. The most abundant product, the tetracyclic pimarane diterpene sphaeropsidin A, was tested for insecticidal effects against the model sucking aphid, Acyrthosiphon pisum. Results showed a toxic dose-dependent oral activity of sphaeropsidin A, with an LC50 of 9.64 mM. Full article
(This article belongs to the Special Issue Current Trends towards Natural Products Synthesis)
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