Identification and Total Synthesis of Novel Fatty Acids from the Siphonarid LimpetSiphonaria denticulata

2001 ◽  
Vol 64 (11) ◽  
pp. 1426-1429 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Heidyleen Cruz ◽  
Craig A. Hill ◽  
James J. De Voss ◽  
Mary Garson
Keyword(s):  
Fatty Acids ◽  
Total Synthesis

scholarly journals First total synthesis of the (±)-2-methoxy-6-heptadecynoic acid and related 2-methoxylated analogs as effective inhibitors of the Leishmania topoisomerase IB enzyme

2012 ◽  
Vol 84 (9) ◽  
pp. 1867-1875 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Michelle Cartagena ◽  
Fengyu Li ◽  
Zhongfang Chen ◽  
Christopher F. Prada ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Total Synthesis ◽  
Leishmania Donovani ◽  
Dna Topoisomerase ◽  
Triple Bonds ◽  
Weak Intermolecular Interactions ◽  
Topoisomerase Ib ◽  
Effective Inhibition ◽  
Acetylenic Fatty Acid

The fatty acids (±)-2-methoxy-6Z-heptadecenoic acid, (±)-2-methoxy-6-hepta-decynoic acid, and (±)-2-methoxyheptadecanoic acid were synthesized and their inhibitory activity against the Leishmania DNA topoisomerase IB enzyme (LdTopIB) determined. Both 2-OMe-17:1 fatty acids were synthesized from 4-bromo-1-pentanol, the olefinic fatty acid in 10 steps and in 7 % overall yield, while the acetylenic fatty acid in 7 steps and in 14 % overall yield. The 2-OMe-17:0 acid was prepared in 6 steps and in 42 % yield from 1-hexa-decanol. The 2-OMe-17:1 acids inhibited LdTopIB, with the acetylenic acid displaying an EC50 = 16.6 ± 1.1 μM, but the 2-OMe-17:0 acid did not inhibit LdTopIB. The (±)-2-methoxy-6Z-heptadecenoic acid preferentially inhibited LdTopIB over the human TopIB enzyme. Unsaturation seems to be a prerequisite for effective inhibition, rationalized in terms of weak intermolecular interactions between the active site of LdTopIB and either the double or triple bonds of the fatty acids. Toxicity toward Leishmania donovani promastigotes was also investigated, resulting in the order acetylenic > olefinic > saturated with the (±)-2-methoxy-6-heptadecynoic acid displaying an EC50 = 74.0 ± 17.1 μM. Our results indicate that α-methoxylation decreases the toxicity of C17:1 fatty acids toward L. donovani promastigotes, but improves their selectivity index.

Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids

2017 ◽  
Vol 82 (15) ◽  
pp. 7832-7838 ◽  
Author(s):  
Shinsuke Inuki ◽  
Ippei Ohta ◽  
Shunichi Ishibashi ◽  
Masayuki Takamatsu ◽  
Koichi Fukase ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Total Synthesis ◽  
Cyclopropane Fatty Acids

Total Synthesis of DHA and DPAn-3 non-enzymatic oxylipins

Synthesis ◽  
2021 ◽  
Author(s):  
alexandre guy ◽  
Jérémy Merad ◽  
Thomas Degrange ◽  
Guillaume Reversat ◽  
Valérie Bultel-Poncé ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Total Synthesis ◽  
Biological Properties ◽  
Chemical Structures ◽  
Structural Variety ◽  
Synthetic Strategy

Oxylipins are formed in-vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentanes, tetrahydrofurans, hydroxylated-PUFA etc.). All structures of oxylipins are of great biological interests. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies and more especially, they were found to have their own biological properties. Produced in-vivo as a non-separable mixture of isomers, total synthesis is a keystone to answer biological questions. In this work, we described the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) using a unique and convergent synthetic strategy.

scholarly journals Mass spectrometry-directed structure elucidation and total synthesis of ultra-long chain (O-acyl)-ω-hydroxy fatty acids

2018 ◽  
Vol 59 (8) ◽  
pp. 1510-1518 ◽  
Author(s):  
Sarah E. Hancock ◽  
Ramesh Ailuri ◽  
David L. Marshall ◽  
Simon H. J. Brown ◽  
Jennifer T. Saville ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Fatty Acids ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Hydroxy Fatty Acids ◽  
Directed Structure ◽  
Long Chain

scholarly journals Quantitation in the regioselectivity of acylation of glycosyl diglycerides: total synthesis of a Streptococcus pneumoniae α-glucosyl diglyceride

2017 ◽  
Vol 53 (6) ◽  
pp. 1100-1103 ◽  
Author(s):  
Mark B. Richardson ◽  
Dylan G. M. Smith ◽  
Spencer J. Williams
Keyword(s):  
Fatty Acids ◽  
Streptococcus Pneumoniae ◽  
Nmr Spectroscopy ◽  
Total Synthesis ◽  
C Nmr

Regioselective fidelity of acylation of glycosyl diacylglycerols can be monitored by use of isotope-labelled fatty acids and quantitative 13C NMR spectroscopy.

Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma

Lipids ◽  
2017 ◽  
Vol 52 (12) ◽  
pp. 1019-1032 ◽  
Author(s):  
Kazuaki Shimada ◽  
Ayako Sugawara ◽  
Toshinobu Korenaga ◽  
Hideki Kawashima
Keyword(s):  
Fatty Acids ◽  
Total Synthesis ◽  
Structural Elucidation

Facile Total Synthesis and Antimicrobial Activity of the Marine Fatty Acids (Z)-2-Methoxy-5-hexadecenoic Acid and (Z)-2-Methoxy-6-hexadecenoic Acid

1998 ◽  
Vol 61 (12) ◽  
pp. 1543-1546 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Anastacio Emiliano ◽  
Norali Hernández-Alonso ◽  
Fernando A. González
Keyword(s):  
Fatty Acids ◽  
Antimicrobial Activity ◽  
Total Synthesis ◽  
Hexadecenoic Acid

ChemInform Abstract: Methods for the Total Synthesis of Acyclic Hydroxylated Fatty Acids

ChemInform ◽  
2010 ◽  
Vol 23 (3) ◽  
pp. no-no
Author(s):  
C. GRAVIER-PELLETIER ◽  
J. DUMAS ◽  
Y. LE MERRER ◽  
J. C. DEPEZAY
Keyword(s):  
Fatty Acids ◽  
Total Synthesis ◽  
Hydroxylated Fatty Acids
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