78217-11-5

Upstream product

• 112-31-2 caprinaldehyde 
• 2425-25-4 O,O-diethyl s-carboethoxymethyl phosphorothioate 
• 623-51-8 ethyl 2-sulfanylacetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 112-30-1 1-Decanol 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 105-36-2 ethyl bromoacetate 
• 1026993-51-0 3-acetoxy-1-ethoxy-1-dodecyne 
• 821-95-4 1-undecene 
• 112-43-6 10-Undecen-1-ol 
• 112-38-9 10-undecenoic acid 
• 51148-67-5 10-undecen-1-yl p-toluenesulfonate 
• 1071-46-1 hydrogen ethyl malonate 

Downstream Products

• 22104-81-0 (2E)-dodec-2-en-1-ol 
• 556068-55-4 (3S,1'S)-3-(N-α-methylbenzyl-N'-benzylamino)-dodecanoate 
• 556068-53-2 ethyl (3R)-3-{benzyl[(1R)-1-phenylethyl]amino}dodecanoate 
• 28254-78-6 (3R)-(-)-3-Hydroxydodecanoic acid 
• 602275-72-9 (4S,1'S)-4-(N-α-methylbenzyl-N'-benzylamino)-1-trimethylsilyl-2-(trimethylsilylmethyl)tridecan-2-ol 
• 602275-71-8 (R)-4-[Benzyl-((R)-1-phenyl-ethyl)-amino]-1-trimethylsilanyl-2-trimethylsilanylmethyl-tridecan-2-ol 
• 20407-84-5 2-dodecenal 
• 1387556-99-1 C₁₉H₃₁N₃O₄S 
• 1387556-98-0 (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate 
• 107796-97-4 (2S,3S)-(3-nonyloxiran-2-yl)methanol 
• 32466-54-9 (E)-2-dodecenoic acid 
• 61621-49-6 2-Nonyl-4,6-dioxo-cyclohexanecarboxylic acid ethyl ester 
• 556068-54-3 methyl (3R)-3-{benzyl[(1R)-1-phenylethyl]amino}dodecanoate 
• 556068-56-5 methyl (3S)-3-{benzyl[(1S)-1-phenylethyl]amino}dodecanoate 

Relevant academic research and scientific papers

Cationic Lipid

The present invention provides a cationic lipid which is able to be used for nucleic acid delivery to the cytoplasm. A cationic lipid according to the present invention is, for example, a compound represented by formula (1) or a pharmaceutically acceptable salt thereof, wherein L1 and L2 independently represent an alkylene group having 3 to 10 carbon atoms; R1 and R2 independently represent an alkyl group having 4 to 24 carbon atoms or an alkenyl group having 4 to 24 carbon atoms; R3 represents an alkyl group having 1 to 3 carbon atoms; and X1 represents a single bond or CO—O—.

Modulation of antibiotic sensitivity and biofilm formation in Pseudomonas aeruginosa by interspecies signal analogues

Pseudomonas aeruginosa, a significant opportunistic pathogen, can participate in inter-species communication through signaling by cis-2-unsaturated fatty acids of the diffusible signal factor (DSF) family. Sensing these signals leads to altered biofilm formation and increased tolerance to various antibiotics, and requires the histidine kinase PA1396. Here, we show that the membrane-associated sensory input domain of PA1396 has five transmembrane helices, two of which are required for DSF sensing. DSF binding is associated with enhanced auto-phosphorylation of PA1396 incorporated into liposomes. Further, we examined the ability of synthetic DSF analogues to modulate or inhibit PA1396 activity. Several of these analogues block the ability of DSF to trigger auto-phosphorylation and gene expression, whereas others act as inverse agonists reducing biofilm formation and antibiotic tolerance, both in vitro and in murine infection models. These analogues may thus represent lead compounds to develop novel adjuvants improving the efficacy of existing antibiotics.

Enantioselective total syntheses of (?)-clavaminol A and deacetyl (+)-clavaminol H

An efficient enantioselective approach to the syntheses of (?)-clavaminol A and deacetyl (+)-clavaminol H is presented, starting from n-decanol. The synthesis features Sharpless asymmetric dihydroxylation (AD), regioselective epoxide formation/opening and α-tosylation as key steps.

Synthesis and evaluation of analogues of the glycinocin family of calcium-dependent antibiotics

The glycinocins are a class of calcium-dependent, acidic cyclolipopeptide antibiotics that are structurally related to the clinically approved antibiotic daptomycin. In this article, we describe the synthesis of a small library of glycinocin analogues that differ by variation in the exocyclic fatty acyl substituent. The glycinocin analogues were screened against a panel of Gram-positive bacteria (as well as Gram-negative P. aeruginosa). These analogues exhibited similar calcium-dependent activity to the parent natural products against Gram-positive bacteria but showed no activity against P. aeruginosa. The length of the fatty acid was shown to be important for optimal biological activity, while the hybridisation at the α,β position and branching within the fatty acyl chain had only subtle effects on activity.

Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases

Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490?nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having a double bond at the α,β-position. These α,β-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decay rate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.

Total synthesis and in vitro bioevaluation of clavaminols A, C, H & deacetyl clavaminol H as potential chemotherapeutic and antibiofilm agents

A highly concise and expedient total synthesis of bioactive clavaminols (1-4) has been executed using commercially available achiral compound decanol. The synthetic strategy relied on trans-Wittig olefination, Sharpless asymmetric epoxidation, regioselective azidolysis and in situ detosylation followed by reduction as key reactions with good overall yield. Based on biological evaluation studies of all the synthesized compounds, it was observed that the clavaminol A (1) exhibited good cytotoxicity against DU145 and SKOV3 cell lines with IC50 value of 10.8 and 12.5 μM, respectively. Clavaminol A (1) and deacetyl clavaminol H (3) displayed selective promising inhibition towards Gram-positive pathogenic bacterial strains and showed good antifungal activity against the tested Candida strains. In addition, compounds 1 and 3 have demonstrated significant bactericidal activity. Compound 3 was found to be equipotent to the standard drug Miconazole displaying MFC value of 15.6 μg/mL against Candida albicans MTCC 854, C. albicans MTCC 1637, C. albicans MTCC 3958 and Candida glabrata MTCC 3019. Compounds 1 and 3 were also able to inhibit the biofilm formation of Micrococcus luteus MTCC 2470 and Staphylococcus aureus MLS16 MTCC 2940. Clavaminol A (1) increased the levels of reactive oxygen species (ROS) accumulation in M. luteus MTCC 2470.

Development of a simple system for the oxidation of electron-rich diazo compounds to ketones

Mild heating of diazo compounds in DMSO furnishes ketone products in moderate to excellent yields. The reaction is particularly effective on electron-rich substrates and exhibits high chemoselectivity, allowing for the use of diazo compounds containing additional oxidation-prone functional groups. This straightforward protocol offers an alternate route to synthetically useful α-ketoesters from readily available aryl diazoacetates.

Photoredox Activation of SF6for Fluorination

We report the first practical use of SF6as a fluorinating reagent in organic synthesis. Photoredox catalysis enables the in situ conversion of SF6, an inert gas, into an active fluorinating species by using visible light. Under these conditions, deoxyfluorination of allylic alcohols is effected with high chemoselectivity and is tolerant of a wide range of functional groups. Application of the methodology in a continuous-flow setup achieves comparable yields to those obtained with a batch setup, while providing drastically increased material throughput of valuable allylic fluoride products.

Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol

We report the total synthesis of (2S,3R)-2-aminododecan-3-ol has been achieved starting from commercially available 10-undecenoic acid. The key steps involved are Sharpless asymmetric epoxidation, Miyashita's boron-directed C-2 regioselective azidolysis, generated the asymmetric centers and in situ detosylation and reduction of azido tosylate. The antifungal activity of the synthesized (2S,3R)-2-aminododecan-3-ol was evaluated on several Candida strains and was comparable to miconazole, a standard drug.

Synthesis of chiral alkenyl epoxides: The sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hübner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy- nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy- nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hübner).