- Assembly of sugars on polystyrene plates: A new facile microarray fabrication technique
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The work presented herein is a new noncovalent glycoarray assembly method for microplates created by simply mixing together an isocyanate-containing C14-hydrocarbon and an amine-containing carbohydrate. 2-Aminoethyl-β-D-galactopyranoside (1) was utilized in model studies and product formation was detected by both ESI-MS and lectin binding. The method has been further extended to array complex carbohydrates.
- Fazio, Fabio,Bryan, Marian C.,Lee, Hing-Ken,Chang, Aileen,Wong, Chi-Huey
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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.
- Citoler, Joan,Finnigan, William,Bevinakatti, Han,Turner, Nicholas J.
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- One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
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The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
- Coeck, Robin,De Vos, Dirk E.
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supporting information
p. 5105 - 5114
(2020/08/25)
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- Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis
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The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.
- Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
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p. 3115 - 3125
(2019/04/26)
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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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- NUCLEOSIDE-MODIFIED RNA FOR INDUCING AN ADAPTIVE IMMUNE RESPONSE
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The present invention generally relates to compositions and methods for inducing an adaptive immune response in a subject. In certain embodiments, the present invention provides a composition comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof. For example, in certain embodiments, the composition comprises a vaccine comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof.
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Page/Page column 115
(2018/05/24)
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- LIPID NANOPARTICLE FORMULATIONS
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Improved formulations of lipid nanoparticles are provided. Use of the lipid nanoparticles for delivery of a therapeutic agent and methods for their preparation are also provided.
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Page/Page column 142-143
(2018/05/24)
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- Tridecyl amine preparation method
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The invention relates to a tridecyl amine preparation method. Methyl myristate serves as a raw material to prepare tetra-acylated azide, Curtius rearrangement reaction and hydrolysis reaction are performed to obtain tridecyl amine, the raw material is low in cost and easy to obtain, reaction conditions are mild, operation difficulty in low, yield is high, and industrial production is facilitated.
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Paragraph 0017; 0018; 0019; 0020
(2018/07/30)
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- NUCLEOSIDE-MODIFIED RNA FOR INDUCING AN ADAPTIVE IMMUNE RESPONSE
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The present invention relates to compositions and methods for inducing adaptive immune response in a subject. In certain embodiments, the present invention provides a composition comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof. For example, in certain embodiments, the composition comprises a vaccine comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof.
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Page/Page column 144
(2016/11/17)
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- NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
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Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.
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Page/Page column 71; 72
(2016/05/02)
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- Electron transfer reduction of nitriles using SmI2-Et 3N-H2O: Synthetic utility and mechanism
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The first general reduction of nitriles to primary amines under single electron transfer conditions is demonstrated using SmI2 (Kagan's reagent) activated with Lewis bases. The reaction features excellent functional group tolerance and represents an attractive alternative to the use of pyrophoric alkali metal hydrides. Notably, the electron transfer from Sm(II) to CN functional groups generates imidoyl-type radicals from bench stable nitrile precursors.
- Szostak, Michal,Sautier, Brice,Spain, Malcolm,Procter, David J.
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supporting information
p. 1092 - 1095
(2014/03/21)
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- Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor
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A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a)ArC-NR and b)ArN-C bonds. This study also highlights the assistance given to these cleavage reactions by the groups attached to N in (a) and to C in (b), by lowering LUMO energies and by stabilizing the products of fragmentation. Radical fragmentations: Electron transfer from the photoactivated neutral electron donor 1 delivers high yields of S-N and C-N cleavage products for a range of nitrogen-containing species. These reactions proceed at room temperature and under mild reaction conditions in the absence of any metal reagents. DMF=N,N-dimethylformamide, Ts=4-toluenesulfonyl.
- O'Sullivan, Steven,Doni, Eswararao,Tuttle, Tell,Murphy, John A.
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supporting information
p. 474 - 478
(2014/01/23)
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- Amino group-containing thiols and method for production thereof
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These amino group-containing mono- or dithiols are represented by formula (I). In order to prepare them, ethylene sulfide is reacted with at least one compound of formula (II), the average number of moles of ethylene sulfide added corresponding to the total m+n, and possibly the compound of formula (I) as obtained is further reacted with ethylene sulfide in order to increase the value of m+n. R1 stands for a straight or branched alkyl or alkenyl group having 10 to 30 carbon atoms; R2 stands for a straight or branched alkyl or alkenyl group having 10 to 30 carbon atoms, or a —(CH2—CH2—S)n—H group; m and n, which are identical or different, each represent 0 or an integer in the range of 1 to 10 and satisfy 1.62 stands for a hydrogen atom in which case R2 in formula (I) will represent —(CH2—CH2—S)n—H, or a straight or branched alkyl or alkenyl group having 10 to 30 carbon atoms, in which case it will remain unchanged in the compound of the formula (I).
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- Thiazoline derivatives
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Object: To provide compounds useful as inhibitors of blood platelet aggregation for intravenous administration. Constitution: A thiazoline derivative represented by the formula: STR1 ?wherein R1 is a hydroxyl group, an alkoxy group, a cycloalkoxy group or a group represented by the formula: R4 NH-- (wherein R4 is a cycloalkyl group), R2 is an alkyl group, a cycloalkyl group or a phenylalkyl group, R3 is a hydrogen atom or an alkyl group, and n is an integer of 2 to 9! or a salt thereof.
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- Heterocyclic hydrazines and hydrazones
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N-carbamoyl-2-carboxyaryl-heterocyclic and hydrazinecarboximidamide-hydrazone derivatives, intermediates and processes for their preparation, agricultural compositions containing them and their use as agricultural chemicals, in particular herbicides.
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