Identification and Total Synthesis of a Novel Dimethylated Fatty Acid from the Caribbean SpongeCalyx podatypa

2000 ◽  
Vol 63 (5) ◽  
pp. 666-669 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Mayra Pagán
Keyword(s):  
Fatty Acid ◽  
Total Synthesis ◽  
The Caribbean

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.

scholarly journals Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange­

SynOpen ◽  
2018 ◽  
Vol 02 (02) ◽  
pp. 0168-0175
Author(s):  
Samuel Shields ◽  
Peter Buist ◽  
Jeffrey Manthorpe
Keyword(s):  
Fatty Acid ◽  
Total Synthesis ◽  
Cyclopropane Ring ◽  
Rapid Quenching ◽  
Cyclopropane Fatty Acid ◽  
Deuterium Incorporation ◽  
Biologically Relevant ◽  
Dihydrosterculic Acid

The total synthesis of isotopically labelled (9R,10S)-dihydro­sterculic acid, a usual cyclopropane fatty acid with biologically relevant toxicity upon desaturation in vivo, is reported. A diastereoselective Corey­–Chaykovsky reaction was employed to form the cyclopropane ring. Rapid quenching of a lithium-sulfoxide exchange was required to achieve the requisite high levels of deuterium incorporation.

scholarly journals Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of syn-β-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone

2019 ◽  
Vol 141 (21) ◽  
pp. 8527-8540 ◽  
Author(s):  
Hugh Nakamura ◽  
Chihiro Tsukano ◽  
Takuma Yoshida ◽  
Motohiro Yasui ◽  
Shinsuke Yokouchi ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Total Synthesis ◽  
Side Chain ◽  
Hydroxyamino Acids ◽  
Scalable Synthesis

Total Synthesis of Methotrexate-γ-TRIS-Fatty Acid Conjugates.

ChemInform ◽  
2003 ◽  
Vol 34 (14) ◽  
Author(s):  
Craig L. Francis ◽  
Qi Yang ◽  
Noel K. Hart ◽  
Fred Widmer ◽  
Michael K. Manthey ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Total Synthesis

scholarly journals First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata

2011 ◽  
Vol 164 (2) ◽  
pp. 113-117 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Nashbly Montano ◽  
Gabriel A. Cintrón ◽  
Carmary Márquez ◽  
Celia Fernández Rubio ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Total Synthesis ◽  
Antileishmanial Activity ◽  
Marine Fatty Acid

Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from Lactobacillus plantarum and identification of its ability to signal through Mincle

2016 ◽  
Vol 52 (72) ◽  
pp. 10902-10905 ◽  
Author(s):  
Sayali Shah ◽  
Masahiro Nagata ◽  
Sho Yamasaki ◽  
Spencer J. Williams
Keyword(s):  
Fatty Acid ◽  
Total Synthesis ◽  
Lactobacillus Plantarum ◽  
Cyclopropane Fatty Acid

Total synthesis of GL1, a complex unsaturated, cyclopropane-containing glycolipid fromLactobacillus plantarumwas accomplished. GL1 and analogues were shown to signal through mouse and human Mincle.

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