76529-42-5Relevant academic research and scientific papers
Radical photocyclization route for macrocyclic lactone ring expansion and conversion to macrocyclic lactams and ketones
Nishikawa, Keisuke,Yoshimi, Yasuharu,Maeda, Kousuke,Morita, Toshio,Takahashi, Ichiro,Itou, Tatsuya,Inagaki, Sho,Hatanaka, Minoru
, p. 582 - 589 (2013)
A new method for the synthesis of macrocyclic lactones, lactams, and ketones, which utilizes photoinduced intramolecular radical cyclization reactions of substrates containing tethered carboxylic acids and α,β-unsaturated carbonyl moieties, has been uncovered. Photocyclization of the carboxylic acids tethered acrylate ester, which were prepared starting from the macrocyclic lactones, gave the two-carbon elongated macrocyclic lactones via decarboxylation. Similar photoreactions of carboxylic acid tethered acryl amide or α,β-unsaturated ketone moieties, which were also prepared starting from the macrocyclic lactones, produced macrocyclic lactams or ketones, respectively. The simple approach can be readily applied to the preparation of a variety of macrocyclic lactones, lactams, and ketones with tunable ring sizes.
Synthesis of wax esters and related trehalose esters from Mycobacterium avium and other mycobacteria
Taher, Salam G.,Al Dulayymi, Juma'a R.,Tima, H. Giresse,Ali, Hanan M.,Romano, Marta,Baird, Mark S.
, p. 3863 - 3876 (2016)
The synthesis of mycobacterial mycolic acid related wax esters and of their trehalose di- and mono-esters is described. The trehalose dimycolates (TDMs) synthesised activated bone marrow derived dendritic cells (BMDCs) in?vitro more strongly than trehalos
Stereoselective synthesis of unsaturated very long chain fatty acid methyl esters
Defretin, Julie,Saez, Jairo,Franck, Xavier,Hocquemiller, Reynald,Figadere, Bruno
, p. 4041 - 4044 (1999)
Very long chain fatty acids are isolated from many different natural sources. However their unsaturated and particularly their diunsaturated derivatives with a Δ(n,n+4) pattern are almost exclusively encountered in marine organisms, until we found some derivatives in the botanical family of the Annonaceae. In this letter we present a very efficient synthesis of this family of products based on the new transition metal-catalyzed coupling reaction between an organomagnesium reagent and a functionalized vinyl bromide.
Synthesis of 23-, 25-, 27-, and 29-Membered (Z)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization
Iwasaki, Tomoya,Tajimi, Yuka,Kameda, Kenta,Kingwell, Callum,Wcislo, William,Osaka, Kazuyuki,Yamawaki, Mugen,Morita, Toshio,Yoshimi, Yasuharu
, p. 8019 - 8026 (2019/06/27)
A new strategy for the synthesis of 23-, 25-, 27-, and 29-membered (Z)-selective unsaturated and saturated macrocyclic lactones from commercially available 16- and 17-membered macrocyclic lactones and bromoalcohols by Wittig reaction, Yamaguchi macrolactonization, and photoinduced decarboxylative radical macrolactonization is described. The position of the unsaturated part in the macrocyclic lactones can be controlled by changing the number of carbons in the starting materials. This protocol can provide facile access to the desired large-ring (Z)-selective unsaturated and saturated macrocyclic lactones from simple starting materials.
Fluorogenic probes to monitor cytosolic phospholipase A2 activity
Ng, Cheng Yang,Kwok, Timothy Xiong Wei,Tan, Francis Chee Kuan,Low, Chian-Ming,Lam, Yulin
supporting information, p. 1813 - 1816 (2017/02/10)
Arachidonic acid derivatives equipped with either one or two fluorescent groups attached to the tip of the alkyl chains were synthesized and shown to function as inhibitor and substrate probes of cPLA2. The inhibitor probe was demonstrated to p
Facile access to arsenic-containing triacylglycerides
Guttenberger, Nikolaus,Sagmeister, Peter,Glabonjat, Ronald A.,Hirner, Stefan,Francesconi, Kevin A.
supporting information, p. 362 - 364 (2017/01/03)
The previously unknown arsenic-containing triacylglycerides (AsTAGs) 3-((15-(dimethylarsinoyl)pentadecanoyl)oxy)propane-1,2-diyl dipalmitate 1 and 2-((15-(dimethylarsinoyl)pentadecanoyl)oxy)propane-1,3-diyl dipalmitate 2 have been synthesized. They will serve as model compounds in the search for naturally occurring AsTAGs, recently proposed natural constituents of fish oils.
Synthetic access to arsenic-containing phosphatidylcholines
Guttenberger, Nikolaus,Glabonjat, Ronald A.,Tassoti, Sebastian,Francesconi, Kevin A.
, p. 2651 - 2653 (2017/06/14)
We wish to disclose the first synthesis of 1-O-hexadecanoyl-2-O-((15-(dimethylarsinoyl)pentadecanoyl)oxy)-sn-glycero-3-phosphocholine, which belongs to the group of arsenic-containing phosphatidylcholines (AsPCs), recently discovered in herring caviar. The synthesized product will serve as a model compound to study biological and toxicological properties of arsenolipids in food.
Lipase-mediated regioselective modifications of macrolactonic sophorolipids
Sembayeva, Aliya,Berhane, Beniam,Carr, Jason A.
, p. 1873 - 1880 (2017/03/11)
Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lip
Mapping the Binding Motifs of Deprotonated Monounsaturated Fatty Acids and Their Corresponding Methyl Esters within Supramolecular Capsules
Wang, Kaiya,Gibb, Bruce C.
, p. 4279 - 4288 (2017/04/27)
A suite of NMR techniques revealed that a cavitand (1) formed 2:1 host-guest complexes with a range of monounsaturated fatty carboxylates and their corresponding methyl esters. All of the carboxylates bound to the capsule in a J-shaped motif with the carboxylate at the equatorial region of the dimeric capsule, and the reverse turn of the chain and the methyl terminal in each polar region of the host. Guest exchange was slow on the NMR time scale, while tumbling was slow or close to the NMR time scale depending on the position and stereochemistry of the double bond. In contrast, the methyl esters were found to bind in three motifs depending on the position and stereochemistry of the double bond. Thus, the esters were observed to bind in a J-shaped, U-shaped (the turn in the guest occupying a polar region and the two termini competing for occupancy of the other pole), or a reverse J-shaped motif (ester moiety and turn each occupying a pole and the methyl terminal located near the equator). Relative binding constant (Krel) determinations revealed that the affinity for the capsule was dependent on the position and stereochemistry of the double bond.
Synthesis of ceramides NS and NP with perdeuterated and specifically ω deuterated N-acyl residues
Sonnenberger, Stefan,Lange, Stefan,Langner, Andreas,Neubert, Reinhard H.H.,Dobner, Bodo
, p. 531 - 542 (2016/11/06)
The synthesis of 12 deuterated ceramides with either a deuteration at the last carbon atom of the amide bound fatty acid or a perdeuterated fatty acid chain is described. The ceramides were prepared starting from sphingosine or phytosphingosine and ω deuterated or perdeuterated fatty acids with PyBOP as activating agent in high yields. For the synthesis of the specifically deuterated fatty acids, dicarboxylic acids were transformed into ω deuterated alkyl bromide, which was chain elongated with blocked ω bromo alcohols by copper catalyzed Grignard coupling. Oxidation of regenerated alcohol function yields the ω deuterated fatty acids.
