Lipids: fatty acids and derivatives, polyketides and isoprenoids

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Editor: Prof. Jeroen S. Dickschat
Universität Bonn
 
Lipids fulfill various functions in life as membrane constituents, for energy storage, or as signaling molecules. If the human lipid metabolism is disturbed, this may lead to serious illnesses such as adipositas and its subsequent complications including cardiovascular diseases or diabetes mellitus. Other consequences of a disordered lipid metabolism include brain dysfunctions, especially if the sphingolipid metabolism is affected, which can often be related to a specific genetic mutation. Sensu stricto, lipids are defined as apolar natural products that can be classified as fatty acids, whose derivatives are waxes, triacylglycerides, phospholipids, sphingolipids and glycolipids. Lipids also constitute important post-translational protein modifications in lipoproteins. The amphiphilic nature of compounds such as phospholipids with a polar headgroup and a long apolar chain results in the spontaneous formation of lipid bilayers in aqueous environments. This was likely a crucial process for the origin of life – and certainly still is for all existing living systems that necessarily contain lipid membranes with their interesting and finely balanced biophysical properties.

See also the Thematic Series:
Natural products in synthesis and biosynthesis II
Transition-metal and organocatalysis in natural product synthesis
Biosynthesis and function of secondary metabolites

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Lipids: fatty acids and derivatives, polyketides and isoprenoids

  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2017, 13, 793–794, doi:10.3762/bjoc.13.78

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Published 27 Apr 2017

Identification, synthesis and mass spectrometry of a macrolide from the African reed frog Hyperolius cinnamomeoventris

  • Markus Menke,
  • Pardha Saradhi Peram,
  • Iris Starnberger,
  • Walter Hödl,
  • Gregory F.M. Jongsma,
  • David C. Blackburn,
  • Mark-Oliver Rödel,
  • Miguel Vences and
  • Stefan Schulz

Beilstein J. Org. Chem. 2016, 12, 2731–2738, doi:10.3762/bjoc.12.269

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Published 13 Dec 2016

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

  • Lukas J. Patalag and
  • Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

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Published 14 Dec 2016

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

  • Naganna Narra,
  • Shiva Shanker Kaki,
  • Rachapudi Badari Narayana Prasad,
  • Sunil Misra,
  • Koude Dhevendar,
  • Venkateshwarlu Kontham and
  • Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

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Published 04 Jan 2017

Posttranslational isoprenylation of tryptophan in bacteria

  • Masahiro Okada,
  • Tomotoshi Sugita and
  • Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

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Published 22 Feb 2017

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

  • Enjuro Harunari,
  • Hisayuki Komaki and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

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Published 08 Mar 2017

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

  • Alexander Bogdanov,
  • Cora Hertzer,
  • Stefan Kehraus,
  • Samuel Nietzer,
  • Sven Rohde,
  • Peter J. Schupp,
  • Heike Wägele and
  • Gabriele M. König

Beilstein J. Org. Chem. 2017, 13, 502–519, doi:10.3762/bjoc.13.50

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Published 13 Mar 2017

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

  • Malte Hilsch,
  • Ivan Haralampiev,
  • Peter Müller,
  • Daniel Huster and
  • Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

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Published 18 Apr 2017

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

  • Katarina Kemper,
  • Max Hirte,
  • Markus Reinbold,
  • Monika Fuchs and
  • Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

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Published 08 May 2017

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

  • Simon Drescher,
  • Vasil M. Garamus,
  • Christopher J. Garvey,
  • Annette Meister and
  • Alfred Blume

Beilstein J. Org. Chem. 2017, 13, 995–1007, doi:10.3762/bjoc.13.99

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Published 23 May 2017

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

  • Stephan Scheeff and
  • Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

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Published 07 Jun 2017

Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

  • Frederik Neuhaus,
  • Fabio Zobi,
  • Gerald Brezesinski,
  • Marta Dal Molin,
  • Stefan Matile and
  • Andreas Zumbuehl

Beilstein J. Org. Chem. 2017, 13, 1099–1105, doi:10.3762/bjoc.13.109

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Published 08 Jun 2017

Strategies in megasynthase engineering – fatty acid synthases (FAS) as model proteins

  • Manuel Fischer and
  • Martin Grininger

Beilstein J. Org. Chem. 2017, 13, 1204–1211, doi:10.3762/bjoc.13.119

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Published 21 Jun 2017

Total synthesis of elansolids B1 and B2

  • Liang-Liang Wang and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2017, 13, 1280–1287, doi:10.3762/bjoc.13.124

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Published 28 Jun 2017

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

  • Ludmila Škorpilová,
  • Silvie Rimpelová,
  • Michal Jurášek,
  • Miloš Buděšínský,
  • Jana Lokajová,
  • Roman Effenberg,
  • Petr Slepička,
  • Tomáš Ruml,
  • Eva Kmoníčková,
  • Pavel B. Drašar and
  • Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

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Published 04 Jul 2017

An improved preparation of phorbol from croton oil

  • Alberto Pagani,
  • Simone Gaeta,
  • Andrei I. Savchenko,
  • Craig M. Williams and
  • Giovanni Appendino

Beilstein J. Org. Chem. 2017, 13, 1361–1367, doi:10.3762/bjoc.13.133

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Published 11 Jul 2017

A new member of the fusaricidin family – structure elucidation and synthesis of fusaricidin E

  • Marcel Reimann,
  • Louis P. Sandjo,
  • Luis Antelo,
  • Eckhard Thines,
  • Isabella Siepe and
  • Till Opatz

Beilstein J. Org. Chem. 2017, 13, 1430–1438, doi:10.3762/bjoc.13.140

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Published 20 Jul 2017

The chemistry and biology of mycolactones

  • Matthias Gehringer and
  • Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

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Published 11 Aug 2017

18-Hydroxydolabella-3,7-diene synthase – a diterpene synthase from Chitinophaga pinensis

  • Jeroen S. Dickschat,
  • Jan Rinkel,
  • Patrick Rabe,
  • Arman Beyraghdar Kashkooli and
  • Harro J. Bouwmeester

Beilstein J. Org. Chem. 2017, 13, 1770–1780, doi:10.3762/bjoc.13.171

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Published 23 Aug 2017

Sulfation and amidinohydrolysis in the biosynthesis of giant linear polyenes

  • Hui Hong,
  • Markiyan Samborskyy,
  • Katsiaryna Usachova,
  • Katharina Schnatz and
  • Peter F. Leadlay

Beilstein J. Org. Chem. 2017, 13, 2408–2415, doi:10.3762/bjoc.13.238

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Published 13 Nov 2017
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