Literature DB >> 27960308

Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid.

Jaron A M Mercer1, Carolyn M Cohen1, Steven R Shuken1, Anna M Wagner1, Myles W Smith1, Frank R Moss1, Matthew D Smith1, Riku Vahala2, Alejandro Gonzalez-Martinez2, Steven G Boxer1, Noah Z Burns1.   

Abstract

Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.

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Year:  2016        PMID： 27960308      PMCID： PMC5279923          DOI： 10.1021/jacs.6b10706

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

1.  Isolation and identification of the irradiation product of thymine.

Authors:  R BEUKERS; W BERENDS
Journal:  Biochim Biophys Acta       Date:  1960-07-15

Review 2.  Anammox bacteria: from discovery to application.

Authors:  J Gijs Kuenen
Journal:  Nat Rev Microbiol       Date:  2008-04       Impact factor: 60.633

3.  Biophysical properties of membrane lipids of anammox bacteria: I. Ladderane phospholipids form highly organized fluid membranes.

Authors:  Henry A Boumann; Marjorie L Longo; Pieter Stroeve; Bert Poolman; Ellen C Hopmans; Marc C A Stuart; Jaap S Sinninghe Damsté; Stefan Schouten
Journal:  Biochim Biophys Acta       Date:  2009-04-17

4.  UV-induced photodimerization of thymine and 5-hydroxymethyluracil in frozen water solutions.

Authors:  D Kaláb
Journal:  Experientia       Date:  1966-01-15

5.  Molecular mechanism of anaerobic ammonium oxidation.

Authors:  Boran Kartal; Wouter J Maalcke; Naomi M de Almeida; Irina Cirpus; Jolein Gloerich; Wim Geerts; Huub J M Op den Camp; Harry R Harhangi; Eva M Janssen-Megens; Kees-Jan Francoijs; Hendrik G Stunnenberg; Jan T Keltjens; Mike S M Jetten; Marc Strous
Journal:  Nature       Date:  2011-10-02       Impact factor: 49.962

6.  Manganese porphyrins catalyze selective C-H bond halogenations.

Authors:  Wei Liu; John T Groves
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

7.  Total synthesis of (+/-)-pentacycloanammoxic acid.

Authors:  Vincent Mascitti; E J Corey
Journal:  J Am Chem Soc       Date:  2004-12-08       Impact factor: 15.419

8.  Ladderane lipid distribution in four genera of anammox bacteria.

Authors:  Jayne E Rattray; Jack van de Vossenberg; Ellen C Hopmans; Boran Kartal; Laura van Niftrik; W Irene C Rijpstra; Marc Strous; Mike S M Jetten; Stefan Schouten; Jaap S Sinninghe Damsté
Journal:  Arch Microbiol       Date:  2008-04-02       Impact factor: 2.552

9.  The membrane bioreactor: a novel tool to grow anammox bacteria as free cells.

Authors:  Wouter R L van der Star; Andreea I Miclea; Udo G J M van Dongen; Gerard Muyzer; Cristian Picioreanu; Mark C M van Loosdrecht
Journal:  Biotechnol Bioeng       Date:  2008-10-01       Impact factor: 4.530

10.  A mixed ladderane/n-alkyl glycerol diether membrane lipid in an anaerobic ammonium-oxidizing bacterium.

Authors:  Jaap S Sinninghe Damsté; W Irene C Rijpstra; Marc Strous; Mike S M Jetten; Olivier R P David; Jan A J Geenevasen; Jan H van Maarseveen
Journal:  Chem Commun (Camb)       Date:  2004-09-30       Impact factor: 6.222
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  14 in total

1.  Ladderane phospholipids form a densely packed membrane with normal hydrazine and anomalously low proton/hydroxide permeability.

Authors:  Frank R Moss; Steven R Shuken; Jaron A M Mercer; Carolyn M Cohen; Thomas M Weiss; Steven G Boxer; Noah Z Burns
Journal:  Proc Natl Acad Sci U S A       Date:  2018-08-27       Impact factor: 11.205

2.  An effective reagent to functionalize alcohols with phosphocholine.

Authors:  Lianyan L Xu; Lawrence J Berg; D Jamin Keith; Steven D Townsend
Journal:  Org Biomol Chem       Date:  2020-01-08       Impact factor: 3.876

3.  Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.

Authors:  Laura K G Ackerman; Jesus I Martinez Alvarado; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2018-10-16       Impact factor: 15.419

4.  A Convenient C-H Functionalization Platform for Pyrroloiminoquinone Alkaloid Synthesis.

Authors:  Myles W Smith; Isaac D Falk; Hideya Ikemoto; Noah Z Burns
Journal:  Tetrahedron       Date:  2019-05-08       Impact factor: 2.457

5.  Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers.

Authors:  Samantha A Green; Suhelen Vásquez-Céspedes; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-07-26       Impact factor: 15.419

6.  Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.

Authors:  Nathan J Line; Brittany P Witherspoon; Erin N Hancock; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-10-06       Impact factor: 15.419

7.  Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Authors:  Erin N Hancock; Erin L Kuker; Dean J Tantillo; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-18       Impact factor: 15.336

8.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005

Review 9.  Ladderane Natural Products: From the Ground Up.

Authors:  Erin N Hancock; M Kevin Brown
Journal:  Chemistry       Date:  2020-10-14       Impact factor: 5.020

10.  Comparative Genomics Analysis of Keratin-Degrading Chryseobacterium Species Reveals Their Keratinolytic Potential for Secondary Metabolite Production.

Authors:  Dingrong Kang; Saeed Shoaie; Samuel Jacquiod; Søren J Sørensen; Rodrigo Ledesma-Amaro
Journal:  Microorganisms       Date:  2021-05-12
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