- Rapid phosphine-free synthesis of CdSe quantum dots: Promoting the generation of Se precursors using a radical initiator
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The replacement of phosphine containing compounds in the synthesis of II-VI quantum dots (QDs) via the 'hot-injection' method has received considerable attention in recent years, in particular toward scaling-up production. A key bottleneck in current appr
- Hou, Bo,Benito-Alifonso, David,Webster, Richard,Cherns, David,Galan, M. Carmen,Fermin, David J.
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Read Online
- Photoinduced remote regioselective radical alkynylation of unactivated C-H bonds
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A method for the remote regioselective alkynylation of unactivated C(sp3)-H bonds in diverse aliphatic amides by photogenerated amidyl radicals has been developed. The site-selectivity is dominated via a 1,5-hydrogen atom transfer (HAT) process of the amide. Mild reaction conditions and high regioselectivity are demonstrated in this methodology.
- Hu, Qu-Ping,Liu, Yong-Ze,Liu, Yu-Tao,Pan, Fei
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p. 2295 - 2298
(2022/02/25)
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- Direct Enzymatic Synthesis of Fatty Amines from Renewable Triglycerides and Oils
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Fatty amines represent an important class of commodity chemicals which have broad applicability in different industries. The synthesis of fatty amines starts from renewable sources such as vegetable oils or animal fats, but the process has multiple drawbacks that compromise the overall effectiveness and efficiency of the synthesis. Herein, we report a proof-of-concept biocatalytic alternative towards the synthesis of primary fatty amines from renewable triglycerides and oils. By coupling a lipase with a carboxylic acid reductase (CAR) and a transaminase (TA), we have accomplished the direct synthesis of multiple medium and long chain primary fatty amines in one pot with analytical yields as high as 97 %. We have also performed a 75 mL preparative scale reaction for the synthesis of laurylamine from trilaurin, obtaining 73 % isolated yield.
- Bevinakatti, Han,Citoler, Joan,Finnigan, William,Turner, Nicholas J.
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- CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF
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Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).
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- Simplifying the Chemical Structure of Cationic Lipids for siRNA-Lipid Nanoparticles
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We report a potent cationic lipid, SST-02 ((3-hydroxylpropyl)dilinoleylamine), which possesses a simple chemical structure and is synthesized just in one step. Cationic lipids are key components of siRNA-lipid nanoparticles (LNP), which may serve as potential therapeutic agents for various diseases. For a decade, chemists have given enhanced potency and new functions to cationic lipids along with structural complexity. In this study, we conducted a medicinal chemistry campaign pursuing chemical simplicity and found that even dilinoleylmethylamine (SST-01) and methylpalmitoleylamine could be used for the in vitro and in vivo siRNA delivery. Further optimization revealed that a hydroxyl group boosted potency, and SST-02 showed an ID50 of 0.02 mg/kg in the factor VII (FVII) model. Rats administered with 3 mg/kg of SST-02 LNP did not show changes in body weight, blood chemistry, or hematological parameters, while the AST level decreased at a dose of 5 mg/kg. The use of SST-02 avoids a lengthy synthetic route and may thus decrease the future cost of nucleic acid therapeutics.
- Kuboyama, Takeshi,Yagi, Kaori,Naoi, Tomoyuki,Era, Tomohiro,Yagi, Nobuhiro,Nakasato, Yoshisuke,Yabuuchi, Hayato,Takahashi, Saori,Shinohara, Fumikazu,Iwai, Hiroto,Koubara-Yamada, Ayumi,Hasegawa, Kazumasa,Miwa, Atsushi
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supporting information
p. 749 - 753
(2019/05/06)
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- A biocatalytic cascade for the conversion of fatty acids to fatty amines
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Fatty amine synthesis from renewable sources is an energetically-demanding process involving toxic metal catalysts and harsh reaction conditions as well as selectivity problems. Herein we present a mild, biocatalytic alternative to the conventional amination of fatty acids through a one-pot tandem cascade performed by a carboxylic acid reductase (CAR) and a transaminase (ω-TA). Saturated and unsaturated fatty acids, with carbon chain lengths ranging from C6 to C18, were successfully aminated obtaining conversions of up to 96%.
- Citoler, Joan,Derrington, Sasha R.,Galman, James L.,Bevinakatti, Han,Turner, Nicholas J.
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supporting information
p. 4932 - 4935
(2019/09/30)
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- Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
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N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
- Lin, Hua,Long, Jonathan Z.,Roche, Alexander M.,Svensson, Katrin J.,Dou, Florence Y.,Chang, Mi Ra,Strutzenberg, Timothy,Ruiz, Claudia,Cameron, Michael D.,Novick, Scott J.,Berdan, Charles A.,Louie, Sharon M.,Nomura, Daniel K.,Spiegelman, Bruce M.,Griffin, Patrick R.,Kamenecka, Theodore M.
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p. 3224 - 3230
(2018/04/23)
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- LIPID NANO PARTICLES COMPRISING COMBINATION OF CATIONIC LIPID
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The present invention provides a lipid nano-particles, which allow nucleic acids to be easily introduced into cells, comprising a cationic lipid represented by formula (I) (wherein: R1 and R2 are, the same or different, alkenyl, etc, and X3 is absent or is alkyl, etc, X1 and X2 are hydrogen atoms, or are combined together to form a single bond or alkylene, and Y1 is absent or anion, L1 is a single bond, etc, R3 is alkyl, etc), and a cationic lipid represented by formula (II) (wherein: R4 and R5 are, the same or different, alkenyl, etc, and X4 and X5 are hydrogen atoms, or are combined together to form a single bond or alkylene, and X6 is absent or is alkyl, etc, Y2 is absent or anion, a and b are, the same or different, 0 to 3, and L4 is a single bond, etc, R6 is alkyl, etc, L2 and L3 are —O—, —CO—O— or —O—CO—), and the like.
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Paragraph 0254; 0261; 0263
(2014/03/21)
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- RNAi PHARMACEUTICAL COMPOSITION FOR SUPPRESSING EXPRESSION OF KRAS GENE
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The present invention provides a composition for suppressing the expression of a KRAS gene, comprising a lipid particle containing, as a drug, a double-stranded nucleic acid having an antisense strand having a sequence of bases complementary to the sequence of at least 19 continuous bases of any one KRAS gene's mRNA of sequence Nos. 1 to 3; and a cationic lipid represented by the following formula (I): wherein R1 and R2, which are the same or different, are each linear or branched alkyl, alkenyl or alkynyl having a carbon number of from 12 to 24; L1 and L2, which are the same or different, are each —CO—O— or —O—CO—; a and b, which are the same or different, are each 1 to 3; and R3 is a hydrogen atom, alkyl having a carbon number of from 1 to 6, or alkenyl having a carbon number of from 3 to 6, and the like.
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Paragraph 0180; 0187; 0189
(2014/03/21)
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- Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
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Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 μM). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 μM).
- Wu, Hui,Kelley, Charles J.,Pino-Figueroa, Alejandro,Vu, Huyen D.,Maher, Timothy J.
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p. 5188 - 5197
(2013/09/02)
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- Process for the preparation of saturated or unsaturated primary fatty amines
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Process for the preparation of unsaturated and saturated primary fatty amines comprising the steps of chlorination, treatment by ammonia, reduction and purification
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Page/Page column 5
(2008/06/13)
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- ACYCLIC SULFAMIDE DERIVATIVES
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The present invention is related to acyclic sulphamide derivatives of formula (I), wherein R1 and R2 may be the same or different, when R1 and R2 are different, R1 is a linear C12-C20 alkyl group or a linear C12-C20 alkenyl group comprising 1, 2, 3 or 4 double bonds; and R2 is a hydrogen atom or a C1-C4 alkyl group, or when R1 and R2 are the same, R1 and R2 are a linear C14-C20 alkyl group or a linear C14-C20 alkenyl group with 1, 2, 3 or 4 double bonds, and pharmaceutically acceptable salts, solvates and hydrates thereof, useful for the manufacture of a medicament for satiety induction and ingestion control, corporal fat modulation and lipidic metabolism regulation and for the manufacture of a medicament for the treatment or prevention of diabetes and cardiovascular diseases. The acyclic sulphamide derivatives are also useful for cosmetic use for reducing subcutaneous fat.
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Page/Page column 22-23
(2008/06/13)
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- UNSATURATED ALIPHATIC PRIMARY AMINE AND PROCESS FOR PRODUCTION THEREOF
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Disclosed is a process for producing an unsaturated aliphatic primary amine which can prevent the by-production of a saturated aliphatic primary amine, can yield a product having no turbidness or no precipitate, and can produce an unsaturated aliphatic primary amine having a low coagulation point with good efficiency. Also disclosed is an unsaturated aliphatic primary amine produced by the process. A process for producing an unsaturated aliphatic primary amine comprising the step of performing the hydrogen reduction of an unsaturated aliphatic nitrile having 16 to 22 carbon atoms with a hydrogenation catalyst in the presence of ammonia, wherein the hydrogen reduction is performed under the conditions where an aromatic carboxylic acid amide is added in an amount of 0.01 to 1.0 part by mass based on 100 parts by mass of the unsaturated aliphatic nitrile and the ratio of the fractional pressure of ammonia to that of hydrogen [(ammonia)/(hydrogen)] is adjusted within the range from 8/2 to 6/4; and an unsaturated aliphatic primary amine produced by the process, which has an amine conversion rate as defined by the formula (1) of 95% or higher, and has an iodine value retention rate as defined by the formula (2) of 95% or higher. [Formula 10] (1) AA Amine conversion rate (%) BB (found amine value of unsaturated aliphatic primary amine) CC (calculated amine value of the amine) [Formula 11] (2) DD Iodine value retention ratio (%) EE (iodine value of unsaturated aliphatic primary amine) × (molecular weight of the amine) FF (iodine value of unsaturated aliphatic nitrile) × (molecular weight of the nitrile)
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Page/Page column 8-12
(2008/06/13)
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- Wetting agent composition for agricultural chemicals
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The present invention provides an agrochemical spreader composition having excellent low-temperature stability. Specifically, the present invention provides an agrochemical spreader composition comprising a surfactant (A) having a melting point of 20 to 60° C., a surfactant (B) having a melting point of not more than 0° C. and water in a specific ratio.
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- Process for producing a primary amine compound
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The present invention relates to a process for producing both of a primary amine compound and an alkylene oxide adduct thereto, given that the both are excellent in color, with high yield. That is, the process comprises hydrogenating a nitrile compound in the presence of a Raney catalyst comprising 90 to 96% by weight of Ni, 3 to 9% by weight of Al and 0.5 to 3% by weight of Mo being based on the total of the atoms of Ni, Al and Mo to obtain the primary amine compound. Further, an alkylene oxide may be added thereto to obtain an alkylene oxide adduct to the primary amine compound.
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