Enantioselective synthesis of mosquito oviposition pheromone and its epimer from a naturally occurring fatty acid

RSC Advances ◽  
2015 ◽  
Vol 5 (123) ◽  
pp. 101732-101739 ◽  
Author(s):  
David Hurem ◽  
Travis Dudding
Keyword(s):  
Fatty Acid ◽  
Late Stage ◽  
Enantioselective Synthesis ◽  
Asymmetric Induction ◽  
Hexadecenoic Acid ◽  
Naturally Occurring ◽  
Mosquito Oviposition ◽  
Asymmetric Transformation

Direct epoxidation of cis-5-hexadecenoic acid towards the synthesis of Mosquito Oviposition Pheromone (MOP) and evaluation of Dynamic Kinetic Asymmetric Transformation (DYKAT) for late-stage asymmetric induction are presented.

Enantioselective Synthesis of Azamerone

2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Selective Synthesis

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

Enantioselective Synthesis of Azamerone

2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Selective Synthesis

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

scholarly journals Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2286
Author(s):  
Gwang-Woo Kim ◽  
Jae-Man Sim ◽  
Yutaka Itabashi ◽  
Min-Jeong Jung ◽  
Joon-Young Jun
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Red Alga ◽  
Proton Nuclear Magnetic Resonance ◽  
Animal Origin ◽  
Monoenoic Acid ◽  
Resonance Spectroscopy ◽  
Hexadecenoic Acid ◽  
Cyclopropane Fatty Acid ◽  
Hexadecanoic Acid

Fatty acids in marine algae have attracted the attention of natural chemists because of their biological activity. The fatty acid compositions of the Solieriaceae families (Rhodophyceae, Gaigartinales) provide interesting information that unusual cyclic fatty acids have been occasionally found. A survey was conducted to profile the characteristic fatty acid composition of the red alga Solieria pacifica (Yamada) Yoshida using gas chromatography-mass spectrometry (GC-MS), infrared spectroscopy (IR), and proton nuclear magnetic resonance spectroscopy (1H-NMR). In S. pacifica, two cyclopentyl fatty acids, 11-cyclopentylundecanoic acid (7.0%), and 13-cyclopentyltridecanoic acid (4.9%), and a cyclopropane fatty acid, cis-11,12-methylene-hexadecanoic acid (7.9%) contributed significantly to the overall fatty acid profile. In particular, this cyclopropane fatty acid has been primarily found in bacteria, rumen microorganisms or foods of animal origin, and has not previously been found in any other algae. In addition, this alga contains a significant amount of the monoenoic acid cis-11-hexadecenoic acid (9.0%). Therefore, cis-11,12-methylene-hexadecanoic acid in S. pacifica was likely produced by methylene addition to cis-11-hexadecenoic acid.

Characterization of Aeromonas genomic species by using quinone, polyamine, and fatty acid patterns

1994 ◽  
Vol 40 (10) ◽  
pp. 844-850 ◽  
Author(s):  
Peter Kämpfer ◽  
Klaus Blasczyk ◽  
Georg Auling
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Octadecenoic Acid ◽  
Hexadecenoic Acid ◽  
Genomic Species ◽  
Great Homogeneity ◽  
Hydroxylated Fatty Acids ◽  
Fatty Acid Patterns ◽  
Chemotaxonomic Study

A chemotaxonomic study was carried out on representative strains of 13 Aeromonas genomic species. Quinone, polyamine, and fatty acid patterns were found to be very useful for an improved characterization of the genus and an improved differentiation from members of the families Enterobacteriaceae and Vibrionaceae. The Q-8-benzoquinone was the predominant ubiquinone, and putrescine and diaminopropane were the major poly amines of the genus. The fatty acid patterns of 181 strains, all characterized by DNA–DNA hybridization, showed a great homogeneity within the genus, with major amounts of hexadecanoic acid (16:0), hexadecenoic acid (16:1), and octadecenoic acid (18:1), and minor amounts of the hydroxylated fatty acids (3-OH 13:0, 2-OH 14:0, 3-OH 14:0) in addition to some iso and anteiso branched fatty acids (i-13:0, i-17:1, i-17:0, and a-17:0). Although some differences in fatty acid profiles between the genomic species could be observed, a clearcut differentiation of all species was not possible.Key words: Aeromonas, polyamines, quinones, fatty acids, differentiation.

Depot fatty acids of Aberdeen Angus and Friesian cattle reared on hay and barley diets

1977 ◽  
Vol 89 (3) ◽  
pp. 575-582 ◽  
Author(s):  
W. M. F. Leat
Keyword(s):  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Stearic Acid ◽  
Acid Composition ◽  
Visual Inspection ◽  
Subcutaneous Fat ◽  
Octadecenoic Acid ◽  
Hexadecenoic Acid ◽  
Friesian Cattle

SummaryAberdeen Angus and Friesian cattle were reared from 4 months of age to slaughter weight at 18–24 months on either high-barley or high-hay diets. Samples of subcutaneous fat were taken by biopsy at 3 monthly intervals, and the degree of fatness of each animal was estimated ultrasonically prior to slaughter, and by visual inspection of the carcasses.The barley-fed animals gained weight more rapidly, and fattened more quickly than the hay-fed animals with the Angus being fatter than the Friesian at the same age. The percentage stearic acid (C18:0) in subcutaneous fat decreased with age and was replaced by octadecenoic acid (C18:l) and hexadecenoic acid (C16:l), these changes being more rapid in barley-fed than in hay-fed animals. At the same degree of fatness the depot fats of the Friesians were more unsaturated than those of the Angus, and in both breeds the fatter the animal the more unsaturated was its depot fat.In the hay-fed cattle the percentage C16:0 in subcutaneous fat increased during the last half of the experiment and at slaughter the percentage C16:0 was significantly higher, and C18:l significantly lower, in all depot fats compared with those of the barley-fed animals.It is concluded that the fatty acid composition of bovine depot fats is modulated by the degree of fattening, and can be affected by diet.

Enantioselective synthesis of (+)-goniodiol and of its naturally occurring acetylated analogs

Tetrahedron ◽  
1996 ◽  
Vol 52 (47) ◽  
pp. 14877-14890 ◽  
Author(s):  
Jean-Philippe Surivet ◽  
Jacques Goré ◽  
Jean-Michel Vatèle
Keyword(s):  
Enantioselective Synthesis ◽  
Naturally Occurring

scholarly journals An evolutionarily ancient Fatty Acid Desaturase is required for the synthesis of hexadecatrienoic acid, which is the main source of the bioactive jasmonate in Marchantia polymorpha

2021 ◽  
Author(s):  
Gonzalo Soriano ◽  
Sophie Kneeshaw ◽  
Guillermo H Jimenez-Aleman ◽  
Angel M. Zamarreno ◽  
Jose Manuel Franco-Zorrilla ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Stress Responses ◽  
Vascular Plants ◽  
Vascular Plant ◽  
Fatty Acid Desaturase ◽  
Marchantia Polymorpha ◽  
Hexadecenoic Acid ◽  
Octadecanoid Pathway ◽  
Low Levels ◽  
Plant Arabidopsis Thaliana

Jasmonates are fatty acid derived hormones that regulate multiple aspects of plant development, growth and stress responses. Bioactive jasmonates, defined as the ligands of the conserved COI1 receptor, differ between vascular plants and bryophytes (using jasmonoyl-L-isoleucine; JA-Ile and dinor-12-oxo-10,15(Z)-phytodienoic acid; dn-OPDA, respectively). Whilst the biosynthetic pathways of JA-Ile in the model vascular plant Arabidopsis thaliana have been elucidated, the details of dn-OPDA biosynthesis in bryophytes are still unclear. Here, we identify an ortholog of Arabidopsis Fatty Acid Desaturase 5 (AtFAD5) in the model liverwort Marchantia polymorpha and show that FAD5 function is ancient and conserved between species separated by more than 450 million years of independent evolution. Similar to AtFAD5, MpFAD5 is required for the synthesis of 7Z-hexadecenoic acid. Consequently, in Mpfad5 mutants the hexadecanoid pathway is blocked, dn-OPDA levels almost completely depleted and normal chloroplast development is impaired. Our results demonstrate that the main source of dn-OPDA in Marchantia is the hexadecanoid pathway and the contribution of the octadecanoid pathway, i.e. from OPDA, is minimal. Remarkably, despite extremely low levels of dn-OPDA, MpCOI1-mediated responses to wounding and insect feeding can still be activated in Mpfad5, suggesting that dn-OPDA is not the only bioactive jasmonate and COI1 ligand in Marchantia.

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