Literature DB >> 25013232

ω-Azido fatty acids as probes to detect fatty acid biosynthesis, degradation, and modification.

Alexander J Pérez1, Helge B Bode1.   

Abstract

FAs play a central role in the metabolism of almost all known cellular life forms. Although GC-MS is regarded as a standard method for FA analysis, other methods, such as HPLC/MS, are nowadays widespread but are rarely applied to FA analysis. Here we present azido-FAs as probes that can be used to study FA biosynthesis (elongation, desaturation) or degradation (β-oxidation) upon their uptake, activation, and metabolic conversion. These azido-FAs are readily accessible by chemical synthesis and their metabolic products can be easily detected after click-chemistry based derivatization with high sensitivity by HPLC/MS, contributing a powerful tool to FA analysis, and hence, lipid analysis in general.
Copyright © 2014 by the American Society for Biochemistry and Molecular Biology, Inc.

Entities:  

Keywords:  S-azidoacyl-N-acetylcysteamine; azido-fatty acids; click-chemistry; cyclooctyne; fatty acid desaturation; fatty acid metabolism; strained promoted cycloadditon; β-oxidation

Mesh:

Substances:

Year:  2014        PMID: 25013232      PMCID: PMC4617356          DOI: 10.1194/jlr.M047969

Source DB:  PubMed          Journal:  J Lipid Res        ISSN: 0022-2275            Impact factor:   5.922


  22 in total

Review 1.  Essentiality of fatty acids.

Authors:  A A Spector
Journal:  Lipids       Date:  1999       Impact factor: 1.880

2.  NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities.

Authors:  Hugo E. Gottlieb; Vadim Kotlyar; Abraham Nudelman
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

3.  A natural prodrug activation mechanism in nonribosomal peptide synthesis.

Authors:  Daniela Reimer; Klaas M Pos; Marco Thines; Peter Grün; Helge B Bode
Journal:  Nat Chem Biol       Date:  2011-09-18       Impact factor: 15.040

4.  Neutral loss fragmentation pattern based screening for arginine-rich natural products in Xenorhabdus and Photorhabdus.

Authors:  Sebastian W Fuchs; Christian C Sachs; Carsten Kegler; Friederike I Nollmann; Michael Karas; Helge B Bode
Journal:  Anal Chem       Date:  2012-08-06       Impact factor: 6.986

5.  Preventing thiol-yne addition improves the specificity of strain-promoted azide-alkyne cycloaddition.

Authors:  Remon van Geel; Ger J M Pruijn; Floris L van Delft; Wilbert C Boelens
Journal:  Bioconjug Chem       Date:  2012-03-08       Impact factor: 4.774

6.  Adaptation to temperature in bacterial membranes.

Authors:  N J Russell
Journal:  Biochem Soc Trans       Date:  1983-08       Impact factor: 5.407

Review 7.  Cu-free click cycloaddition reactions in chemical biology.

Authors:  John C Jewett; Carolyn R Bertozzi
Journal:  Chem Soc Rev       Date:  2010-04       Impact factor: 54.564

8.  A new Escherichia coli metabolic competency: growth on fatty acids by a novel anaerobic beta-oxidation pathway.

Authors:  John W Campbell; Rachael M Morgan-Kiss; John E Cronan
Journal:  Mol Microbiol       Date:  2003-02       Impact factor: 3.501

Review 9.  Tandem mass spectrometry in the study of fatty acids, bile acids, and steroids.

Authors:  William J Griffiths
Journal:  Mass Spectrom Rev       Date:  2003 Mar-Apr       Impact factor: 10.946

10.  Identification and functional expression of a Delta9-fatty acid desaturase from Psychrobacter urativorans in Escherichia coli.

Authors:  Yan Li; Matthias Dietrich; Rolf D Schmid; Bingfang He; Pingkai Ouyang; Vlada B Urlacher
Journal:  Lipids       Date:  2008-02-07       Impact factor: 1.880

View more
  2 in total

Review 1.  Interrogating Plant-Microbe Interactions with Chemical Tools: Click Chemistry Reagents for Metabolic Labeling and Activity-Based Probes.

Authors:  Vivian S Lin
Journal:  Molecules       Date:  2021-01-05       Impact factor: 4.411

2.  Live-Cell Imaging of Sterculic Acid-a Naturally Occurring 1,2-Cyclopropene Fatty Acid-by Bioorthogonal Reaction with Turn-On Tetrazine-Fluorophore Conjugates.

Authors:  Kristine Bertheussen; Merel van de Plassche; Thomas Bakkum; Berend Gagestein; Iakovia Ttofi; Alexi J C Sarris; Herman S Overkleeft; Mario van der Stelt; Sander I van Kasteren
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.