- Transaminase-Mediated Amine Borrowing via Shuttle Biocatalysis
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Shuttle catalysis has emerged as a useful methodology for the reversible transfer of small functional groups, such as CO and HCN, and goes far beyond transfer hydrogenation chemistry. While a biocatalytic hydrogen-borrowing methodology is well established, the biocatalytic borrowing of alternative functional groups has not yet been realized. Herein, we present a new concept of amine borrowing via biocatalytic shuttle catalysis, which has no counterpart in chemo-shuttle catalysis and allows efficient intermolecular amine shuttling to generate reactive intermediates in situ. By coupling this dynamic exchange with an irreversible downstream step to displace the reaction equilibrium in the forward direction, high conversion to target products can be achieved. We showcase the potential of this amine-borrowing methodology using a biocatalytic equivalent of both the Knorr-pyrrole synthesis and Pictet-Spengler reaction.
- O'Reilly, Elaine,O'Sullivan, Rachel,Ryan, James,Taday, Freya
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supporting information
(2022/01/04)
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- Fragment-Based Drug Discovery of Potent Protein Kinase C Iota Inhibitors
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Protein kinase C iota (PKC-i) is an atypical kinase implicated in the promotion of different cancer types. A biochemical screen of a fragment library has identified several hits from which an azaindole-based scaffold was chosen for optimization. Driven by a structure-activity relationship and supported by molecular modeling, a weakly bound fragment was systematically grown into a potent and selective inhibitor against PKC-i.
- Kwiatkowski, Jacek,Liu, Boping,Tee, Doris Hui Ying,Chen, Guoying,Ahmad, Nur Huda Binte,Wong, Yun Xuan,Poh, Zhi Ying,Ang, Shi Hua,Tan, Eldwin Sum Wai,Ong, Esther Hq,Nurul, Dinie,Poulsen, Anders,Pendharkar, Vishal,Sangthongpitag, Kanda,Lee, May Ann,Sepramaniam, Sugunavathi,Ho, Soo Yei,Cherian, Joseph,Hill, Jeffrey,Keller, Thomas H.,Hung, Alvin W.
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p. 4386 - 4396
(2018/05/31)
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- A 3 - (2 - amino-propyl) phenol preparation method (by machine translation)
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The invention discloses a 3 - (2 - amino-propyl) phenol preparation method, in order to methoxy bromophenylacetic, epoxy propane, methyl sulfonic acid, ammonia methanol and hydrobromic acid as the raw materials, through the four-step reaction to obtain the target product 3 - (2 - amino-propyl) phenol. The invention has simple operation, environment friendly, comprehensive yield is 63% more, than the existing 35.6% yield, with a remarkable enhancement, greatly reduces the production cost of the existing drugs, is suitable for industrial scale production. (by machine translation)
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Paragraph 0041; 0042; 0043; 0055; 0056; 0069; 0070
(2017/08/28)
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- Catalytic N-sulfonyliminium ion-mediated cyclizations to α-vinyl-substituted isoquinolines and β-carbolines and applications in metathesis
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Catalytic Sn(OTf)2-induced cyclization of linear, aryl-containing allylic N,O-acetals produced vinyl-substituted tetrahydroisoquinolines and tetrahydro-1H-β-carbolines. The usefulness of the vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks for alkaloid structures. The α-vinyl moiety was utilized in a [2,3] sigmatropic rearrangement, in ring-closing metathesis and a cross-metathesis-based synthesis of vincantril, an antianoxia agent, and a synthetic member of the vincamine type natural products.
- Kinderman, Sape S.,Wekking, Monique M. T.,Van Maarseveen, Jan H.,Schoemaker, Hans E.,Hiemstra, Henk,Rutjes, Floris P. J. T.
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p. 5519 - 5527
(2007/10/03)
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- CAL-B-catalyzed resolution of some pharmacologically interesting β-substituted isopropylamines
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Some pharmacologically active amines such as amphetamine, the isomeric o-, m- and p-methoxyamphetamines, 4-phenylbutan-2-amine and mexiletine, as well as their corresponding acetamides, have been prepared in high yields and with very high enantiomeric excesses. The method consists of the Candida antarctica lipase B (CAL-B)-mediated enantioselective acetylation of racemic amines using ethyl acetate as solvent and acyl donor. The enzyme follows Kazlauskas' rule with all amines, (R)-amides being obtained as the major enantiomer in all cases. From the conversion values measured for both enantiomers, it can be deduced that the size of the substituents attached to the stereocenter is responsible for the enantioselectivity and rate of some of these reactions.
- Gonzalez-Sabin, Javier,Gotor, Vicente,Rebolledo, Francisca
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p. 1315 - 1320
(2007/10/03)
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- Photoinduced nucleophilic addition of ammonia and alkylamines to methoxy-substituted styrene derivatives
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The photoamination of trans-1-arylpropenes (aryl = 2-methoxyphenyl), (1), 3-methoxyphenyl (2) 3,4-dimethoxyphenyl (3), and 4-methoxyphenyl (4) with NH3, i-PrNH2, and t-BuNH2 (RNH2), in the presence of p-dicyanobenzene (p-DCB) gave 2-alkylamino-1 arylpropanes (9) and/or 2-alkylamino-1-aryl-1-(4-cyanophenyl)propanes (10). The photoaminations of 1,2-dihydro-7-methoxynaphthalenes (6-8) with RNH2 in the presence of p-DCB gave mainly 2-alkylamino-1-(4-cyanophenyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene s (13). The photoamination of trans-1-(3,5-dimethoxyphenyl)propene (5) with i-PrNH2 occurred at aromatic ring to give trans-1-(2-isopropylamino-3,5-dimethoxyphenyl)propene (11). The photoaminations of 1-4 and 6-8 with NH3 in the presence of m-dicyanobenzene gave the aminated products without incorporation of cyanophenyl group. Furthermore, the addition of 1,3,5-triphenylbenzene and m-terphenyl for these reactions improved the yields of the photoaminated products.
- Yamashita,Yamashita, Toshiaki,Yasuda,Yasuda, Masahide,Isami,Isami, Toshihiro,Tanabe,Tanabe, Kimiko,Shima,Shima, Kensuke
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p. 9275 - 9286
(2007/10/02)
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- Synthesis of phenethylamine moiety by photoamination of styrene derivatives with ammonia
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The photoaminations of trans-1-arylpropenes and 7-methoxy-1,2-dihydronaphthalenes with ammonia in the presence of dicyanobenzene gave 1-aryl-2-propylamines and 2-amino-6-methoxy-1,2,3,4-tetrahydronaphthalenes, respectively. The yields of the aminated compounds were improved by the addition of 1,3,5-triphenylbenzene or m-terphenyl.
- Yamashita, Toshiaki,Yasuda, Masabide,Isami, Toshihiro,Nakano, Shozo,Tanabe, Kimiko,Shima, Kensuke
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p. 5131 - 5134
(2007/10/02)
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- Methods for the treatment of hypertension
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Acetylene compounds of the formula (I): STR1 wherein Y, R1, R2, R3, and R4 are as described herein, m is 0-3, n is 0-2 and Ar is phenyl or an aromatic heterocycle are disclosed. The compounds possess antihyperte
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- 3,10-Dimethoxyprotoberberines
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Protoberberines with the unusual 3,10-dimethoxy substitution are synthesized by photocyclization of E- and Z-1-ethylidene-1,2,3,4-tetrahydro-6-methoxy-2-(3-methoxybenzoyl)isoquinolines.
- Chinnasamy, Pennamuthiriar,Iwasa, Kinuko,Angerer, Silvia von,Weimar, Christian,Wiegrebe, Wolfgang
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p. 790 - 798
(2007/10/02)
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- Aralykyl (arylethynyl)aralkyl amines and their use as vasodilators and antihypertensives
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Acetylenes of the formula (I): STR1 wherein Y, m, R1, R2 q, Alk, R3, n and R4 are as defined herein and Ar1 and Ar2 are aromatic, including the salts and ammonium derivatives of formula (I), in treating angina, hypertension and cardiac arrhythmias. Pharmaceutical compositions, methods of use and synthesis and novel intermediates are also part of the invention.
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