25876-34-0Relevant academic research and scientific papers
Direct Enzymatic Synthesis of Fatty Amines from Renewable Triglycerides and Oils
Citoler, Joan,Finnigan, William,Bevinakatti, Han,Turner, Nicholas J.
, (2021/11/30)
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.
Method for preparing amine compound by reducing amide compound
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Paragraph 0289-0291, (2021/02/10)
The invention relates to a method for preparing an amine compound by reducing an amide compound, which comprises the following steps: in a protective atmosphere, mixing the amide compound or cyclic amide, a zirconium metal catalyst and pinacol borane, carrying out amide reduction reaction at room temperature, and carrying out aftertreatment by using an ether solution of hydrogen chloride after 12-48 hours to obtain an amine hydrochloride compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate range.
Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application
Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong
, p. 2059 - 2067 (2021/09/02)
Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.
A biocatalytic cascade for the conversion of fatty acids to fatty amines
Citoler, Joan,Derrington, Sasha R.,Galman, James L.,Bevinakatti, Han,Turner, Nicholas J.
supporting information, p. 4932 - 4935 (2019/09/30)
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%.
Simplifying the Chemical Structure of Cationic Lipids for siRNA-Lipid Nanoparticles
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
supporting information, p. 749 - 753 (2019/05/06)
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.
DELIVERY MOLECULES FOR THERAPEUTICS
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Paragraph 0317, (2017/08/26)
Activity-generating delivery molecules comprising the structure R3—(C═O)-Xaa-NH—R4 wherein Xaa is any D- or L-amino acid residue with a non-hydrogen, substituted or unsubstituted side chain, R3—(C═O)— and —NH—R4 are independently a long chain group, each long chain group containing one or more carbon-carbon double bonds, and salts, compositions and methods of use thereof. The activity-generating delivery compounds and compositions are useful for generating activity of an active agent in a cell, tissue, or subject.
IMPROVED COMPOSITIONS AND METHODS FOR THE DELIVERY OF NUCLEIC ACIDS
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Paragraph 0251;0253, (2016/08/17)
The present invention provides compositions and methods for the delivery of therapeutic agents to cells. In particular, these include novel lipids and nucleic acid-lipid particles that provide efficient encapsulation of nucleic acids and efficient delivery of the encapsulated nucleic acid to cells in vivo. The compositions of the present invention are highly potent, thereby allowing effective knock-down of specific target protein at relatively low doses. In addition, the compositions and methods of the present invention are less toxic and provide a greater therapeutic index compared to compositions and methods previously known in the art.
LIPID NANO PARTICLES COMPRISING COMBINATION OF CATIONIC LIPID
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Paragraph 0254; 0261, (2014/03/21)
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.
RNAi PHARMACEUTICAL COMPOSITION FOR SUPPRESSING EXPRESSION OF KRAS GENE
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Paragraph 0180; 0187, (2014/03/21)
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.
CATIONIC LIPID
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Paragraph 0163, (2014/10/16)
The present invention provides a cationic lipid and the like. The cationic lipid is for delivering a medicament containing a cationic lipid which facilitates the introduction of a nucleic acid into a cell or the like, and is represented by formula (I). In the formula, R1 is linear or branched alkyl, alkenyl, or alkynyl, each having 8 to 24 carbon atoms, R2 is linear or branched alkyl, alkenyl, or alkynyl, each having 8 to 24 carbon atoms, or alkoxyethylene, alkoxypropylene, alkenyloxyethylene, alkenyloxypropylene, alkynyloxyethylene, or alkynyloxypropylene, R3 and R4 may be the same or different, and are each alkyl having 1 to 3 carbon atoms or are combined together to form alkylene having 2 to 6 carbon atoms, or R3 and R5 are combined together to form alkylene having 2 to 6 carbon atoms, R5 is a hydrogen atom, alkyl having 1 to 6 carbon atoms, alkenyl having 3 to 6 carbon atoms, amino, monoalkylamino, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, or the like, or is combined together with R3 to form alkylene having 2 to 6 carbon atoms, X is alkylene having 1 to 6 carbon atoms, and Y is a single bond, alkylene having 1 to 6 carbon atoms, or the like.
