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Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism.

The Journal of organic chemistry

Jia KY, Yu JB, Jiang ZJ, Su WK.
PMID: 27328874
J Org Chem. 2016 Jul 15;81(14):6049-55. doi: 10.1021/acs.joc.6b01138. Epub 2016 Jul 06.

Construction of 3-vinylindoles (3) and β,β-diindolyl propionates (4) through solvent-free C-H functionalization has been explored under high-speed ball-milling conditions. The reaction selectivity is influenced by the catalyst dramatically: Pd(OAc)2 provides 3 in moderate to good yields, whereas PdX2 (X...

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Jia KY, Yu JB, Jiang ZJ, et al. Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism. J Org Chem. 2016;81(14):6049-55doi: 10.1021/acs.joc.6b01138.
Jia, K. Y., Yu, J. B., Jiang, Z. J., & Su, W. K. (2016). Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism. The Journal of organic chemistry, 81(14), 6049-55. https://doi.org/10.1021/acs.joc.6b01138
Jia, Kan-Yan, et al. "Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism." The Journal of organic chemistry vol. 81,14 (2016): 6049-55. doi: https://doi.org/10.1021/acs.joc.6b01138
Jia KY, Yu JB, Jiang ZJ, Su WK. Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism. J Org Chem. 2016 Jul 15;81(14):6049-55. doi: 10.1021/acs.joc.6b01138. Epub 2016 Jul 06. PMID: 27328874.
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Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates.

The Journal of organic chemistry

Pradhan TR, Mendhekar KL, Mohapatra DK.
PMID: 25941839
J Org Chem. 2015 Jun 05;80(11):5517-31. doi: 10.1021/acs.joc.5b00400. Epub 2015 May 20.

The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are...

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Pradhan TR, Mendhekar KL, Mohapatra DK. Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates. J Org Chem. 2015;80(11):5517-31doi: 10.1021/acs.joc.5b00400.
Pradhan, T. R., Mendhekar, K. L., & Mohapatra, D. K. (2015). Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates. The Journal of organic chemistry, 80(11), 5517-31. https://doi.org/10.1021/acs.joc.5b00400
Pradhan, Tapas R, et al. "Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates." The Journal of organic chemistry vol. 80,11 (2015): 5517-31. doi: https://doi.org/10.1021/acs.joc.5b00400
Pradhan TR, Mendhekar KL, Mohapatra DK. Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates. J Org Chem. 2015 Jun 05;80(11):5517-31. doi: 10.1021/acs.joc.5b00400. Epub 2015 May 20. PMID: 25941839.
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Chichibabin indolizine synthesis revisited: synthesis of indolizinones by solvolysis of 4-alkoxycarbonyl-3-oxotetrahydroquinolizinium ylides.

The Journal of organic chemistry

Kostik EI, Abiko A, Oku A.
PMID: 11304179
J Org Chem. 2001 Apr 20;66(8):2618-23. doi: 10.1021/jo0011639.

Solvolysis of 4-alkoxycarbonyl-(or 4-acyl)-3-oxo-1,2,3,4-tetrahydroquinolizinium ylides (1-4) was studied and three types of reactions were found to proceed competitively. Thus, alcoholysis afforded the Chichibabin rearrangement products, 2,3-dihydro-2-indolizinones (5-8), solvolysis in trifluoroethanol or in aqueous methanol caused ring opening (and subsequent...

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Kostik EI, Abiko A, Oku A. Chichibabin indolizine synthesis revisited: synthesis of indolizinones by solvolysis of 4-alkoxycarbonyl-3-oxotetrahydroquinolizinium ylides. J Org Chem. 2001;66(8):2618-23doi: 10.1021/jo0011639.
Kostik, E. I., Abiko, A., & Oku, A. (2001). Chichibabin indolizine synthesis revisited: synthesis of indolizinones by solvolysis of 4-alkoxycarbonyl-3-oxotetrahydroquinolizinium ylides. The Journal of organic chemistry, 66(8), 2618-23. https://doi.org/10.1021/jo0011639
Kostik, E I, et al. "Chichibabin indolizine synthesis revisited: synthesis of indolizinones by solvolysis of 4-alkoxycarbonyl-3-oxotetrahydroquinolizinium ylides." The Journal of organic chemistry vol. 66,8 (2001): 2618-23. doi: https://doi.org/10.1021/jo0011639
Kostik EI, Abiko A, Oku A. Chichibabin indolizine synthesis revisited: synthesis of indolizinones by solvolysis of 4-alkoxycarbonyl-3-oxotetrahydroquinolizinium ylides. J Org Chem. 2001 Apr 20;66(8):2618-23. doi: 10.1021/jo0011639. PMID: 11304179.
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Organic acids for performance enhancement in pig diets.

Nutrition research reviews

Partanen KH, Mroz Z.
PMID: 19087448
Nutr Res Rev. 1999 Jun;12(1):117-45. doi: 10.1079/095442299108728884.

Organic acids and their salts appear to be potential alternatives to prophylactic in-feed antibiotics and growth promoters in order to improve the performance of weaned piglets, fattening pigs and reproductive sows, although their growth-promoting effects are generally less than...

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Partanen KH, Mroz Z. Organic acids for performance enhancement in pig diets. Nutr Res Rev. 1999;12(1):117-45doi: 10.1079/095442299108728884.
Partanen, K. H., & Mroz, Z. (1999). Organic acids for performance enhancement in pig diets. Nutrition research reviews, 12(1), 117-45. https://doi.org/10.1079/095442299108728884
Partanen, K H, and Mroz, Z. "Organic acids for performance enhancement in pig diets." Nutrition research reviews vol. 12,1 (1999): 117-45. doi: https://doi.org/10.1079/095442299108728884
Partanen KH, Mroz Z. Organic acids for performance enhancement in pig diets. Nutr Res Rev. 1999 Jun;12(1):117-45. doi: 10.1079/095442299108728884. PMID: 19087448.
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Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

Tetrahedron letters

Fu TH, Bonaparte A, Martin SF.
PMID: 20161309
Tetrahedron Lett. 2009 Jul 01;50(26):3253-3257. doi: 10.1016/j.tetlet.2009.02.018.

A variety of heterocyclic alcohols and acetates were coupled with silyl ketene acetals and other π-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array of substituted β-heteroaryl propionates, including those with contiguous quaternary centers, as well as...

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Fu TH, Bonaparte A, Martin SF. Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles. Tetrahedron Lett. 2009;50(26):3253-3257doi: 10.1016/j.tetlet.2009.02.018.
Fu, T. H., Bonaparte, A., & Martin, S. F. (2009). Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles. Tetrahedron letters, 50(26), 3253-3257. https://doi.org/10.1016/j.tetlet.2009.02.018
Fu, Tsung-Hao, et al. "Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles." Tetrahedron letters vol. 50,26 (2009): 3253-3257. doi: https://doi.org/10.1016/j.tetlet.2009.02.018
Fu TH, Bonaparte A, Martin SF. Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles. Tetrahedron Lett. 2009 Jul 01;50(26):3253-3257. doi: 10.1016/j.tetlet.2009.02.018. PMID: 20161309; PMCID: PMC2699308.
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Three-dimensional structure of cytochrome c' from two Alcaligenes species and the implications for four-helix bundle structures.

Acta crystallographica. Section D, Biological crystallography

Dobbs AJ, Anderson BF, Faber HR, Baker EN.
PMID: 15299707
Acta Crystallogr D Biol Crystallogr. 1996 Mar 01;52:356-68. doi: 10.1107/S0907444995008328.

The three-dimensional structures of two cytochromes c' have been determined in order to analyse the common features of proteins of this family and their relationship with other four-helix bundle structures. The structure of cytochrome c' from Alcaligenes sp was...

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Dobbs AJ, Anderson BF, Faber HR, et al. Three-dimensional structure of cytochrome c' from two Alcaligenes species and the implications for four-helix bundle structures. Acta Crystallogr D Biol Crystallogr. 1996;52:356-68doi: 10.1107/S0907444995008328.
Dobbs, A. J., Anderson, B. F., Faber, H. R., & Baker, E. N. (1996). Three-dimensional structure of cytochrome c' from two Alcaligenes species and the implications for four-helix bundle structures. Acta crystallographica. Section D, Biological crystallography, 52356-68. https://doi.org/10.1107/S0907444995008328
Dobbs, A J, et al. "Three-dimensional structure of cytochrome c' from two Alcaligenes species and the implications for four-helix bundle structures." Acta crystallographica. Section D, Biological crystallography vol. 52 (1996): 356-68. doi: https://doi.org/10.1107/S0907444995008328
Dobbs AJ, Anderson BF, Faber HR, Baker EN. Three-dimensional structure of cytochrome c' from two Alcaligenes species and the implications for four-helix bundle structures. Acta Crystallogr D Biol Crystallogr. 1996 Mar 01;52:356-68. doi: 10.1107/S0907444995008328. PMID: 15299707.
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Redox Cofactor Rotates during Its Stepwise Decarboxylation: Molecular Mechanism of Conversion of Coproheme to Heme .

ACS catalysis

Milazzo L, Gabler T, Pühringer D, Jandova Z, Maresch D, Michlits H, Pfanzagl V, Djinović-Carugo K, Oostenbrink C, Furtmüller PG, Obinger C, Smulevich G, Hofbauer S.
PMID: 31423350
ACS Catal. 2019 Aug 02;9(8):6766-6782. doi: 10.1021/acscatal.9b00963. Epub 2019 Jun 18.

Coproheme decarboxylase (ChdC) catalyzes the last step in the heme biosynthesis pathway of monoderm bacteria with coproheme acting both as redox cofactor and substrate. Hydrogen peroxide mediates the stepwise decarboxylation of propionates 2 and 4 of coproheme. Here we...

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Milazzo L, Gabler T, Pühringer D, et al. Redox Cofactor Rotates during Its Stepwise Decarboxylation: Molecular Mechanism of Conversion of Coproheme to Heme . ACS Catal. 2019;9(8):6766-6782doi: 10.1021/acscatal.9b00963.
Milazzo, L., Gabler, T., Pühringer, D., Jandova, Z., Maresch, D., Michlits, H., Pfanzagl, V., Djinović-Carugo, K., Oostenbrink, C., Furtmüller, P. G., Obinger, C., Smulevich, G., & Hofbauer, S. (2019). Redox Cofactor Rotates during Its Stepwise Decarboxylation: Molecular Mechanism of Conversion of Coproheme to Heme . ACS catalysis, 9(8), 6766-6782. https://doi.org/10.1021/acscatal.9b00963
Milazzo, Lisa, et al. "Redox Cofactor Rotates during Its Stepwise Decarboxylation: Molecular Mechanism of Conversion of Coproheme to Heme ." ACS catalysis vol. 9,8 (2019): 6766-6782. doi: https://doi.org/10.1021/acscatal.9b00963
Milazzo L, Gabler T, Pühringer D, Jandova Z, Maresch D, Michlits H, Pfanzagl V, Djinović-Carugo K, Oostenbrink C, Furtmüller PG, Obinger C, Smulevich G, Hofbauer S. Redox Cofactor Rotates during Its Stepwise Decarboxylation: Molecular Mechanism of Conversion of Coproheme to Heme . ACS Catal. 2019 Aug 02;9(8):6766-6782. doi: 10.1021/acscatal.9b00963. Epub 2019 Jun 18. PMID: 31423350; PMCID: PMC6691569.
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Inhibition of Clostridium botulinum 62A by Saturated n-Aliphatic Acids, n-Alkyl Formates, Acetates, Propionates and Butyrates.

Journal of food protection

Dymicky M, Trenchard H.
PMID: 30913718
J Food Prot. 1982 Oct;45(12):1117-1119. doi: 10.4315/0362-028X-45.12.1117.

Saturated aliphatic acids (C

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Dymicky M, Trenchard H. Inhibition of Clostridium botulinum 62A by Saturated n-Aliphatic Acids, n-Alkyl Formates, Acetates, Propionates and Butyrates. J Food Prot. 1982;45(12):1117-1119doi: 10.4315/0362-028X-45.12.1117.
Dymicky, M., & Trenchard, H. (1982). Inhibition of Clostridium botulinum 62A by Saturated n-Aliphatic Acids, n-Alkyl Formates, Acetates, Propionates and Butyrates. Journal of food protection, 45(12), 1117-1119. https://doi.org/10.4315/0362-028X-45.12.1117
Dymicky, M, and Trenchard, H. "Inhibition of Clostridium botulinum 62A by Saturated n-Aliphatic Acids, n-Alkyl Formates, Acetates, Propionates and Butyrates." Journal of food protection vol. 45,12 (1982): 1117-1119. doi: https://doi.org/10.4315/0362-028X-45.12.1117
Dymicky M, Trenchard H. Inhibition of Clostridium botulinum 62A by Saturated n-Aliphatic Acids, n-Alkyl Formates, Acetates, Propionates and Butyrates. J Food Prot. 1982 Oct;45(12):1117-1119. doi: 10.4315/0362-028X-45.12.1117. PMID: 30913718.
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Synthesis, Characterization, and in vivo Distribution of Intracellular Delivered Macrolide Short-Chain Fatty Acid Derivatives.

ChemMedChem

Straß S, Schwamborn A, Keppler M, Cloos N, Guezguez J, Guse JH, Burnet M, Laufer S.
PMID: 33787081
ChemMedChem. 2021 Jul 20;16(14):2254-2269. doi: 10.1002/cmdc.202100139. Epub 2021 May 11.

Short-chain fatty acids (SCFAs) have a range of effects in metabolism and immune regulation. We have observed that delivery of SCFAs to lysosomes has potent immune regulatory effects, possibly as a surrogate signal for the presence of anaerobic organisms....

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Straß S, Schwamborn A, Keppler M, et al. Synthesis, Characterization, and in vivo Distribution of Intracellular Delivered Macrolide Short-Chain Fatty Acid Derivatives. ChemMedChem. 2021;16(14):2254-2269doi: 10.1002/cmdc.202100139.
Straß, S., Schwamborn, A., Keppler, M., Cloos, N., Guezguez, J., Guse, J. H., Burnet, M., & Laufer, S. (2021). Synthesis, Characterization, and in vivo Distribution of Intracellular Delivered Macrolide Short-Chain Fatty Acid Derivatives. ChemMedChem, 16(14), 2254-2269. https://doi.org/10.1002/cmdc.202100139
Straß, Simon, et al. "Synthesis, Characterization, and in vivo Distribution of Intracellular Delivered Macrolide Short-Chain Fatty Acid Derivatives." ChemMedChem vol. 16,14 (2021): 2254-2269. doi: https://doi.org/10.1002/cmdc.202100139
Straß S, Schwamborn A, Keppler M, Cloos N, Guezguez J, Guse JH, Burnet M, Laufer S. Synthesis, Characterization, and in vivo Distribution of Intracellular Delivered Macrolide Short-Chain Fatty Acid Derivatives. ChemMedChem. 2021 Jul 20;16(14):2254-2269. doi: 10.1002/cmdc.202100139. Epub 2021 May 11. PMID: 33787081.
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Influence of heme propionates on the nitrite reductase activity of myoglobin.

Journal of inorganic biochemistry

Galinato MGI, Trail AM, Steinbeck OR, Si Z, Rodland AM, Gowen J.
PMID: 34688205
J Inorg Biochem. 2022 Jan;226:111630. doi: 10.1016/j.jinorgbio.2021.111630. Epub 2021 Oct 16.

The heme propionates in myoglobin (Mb) form a H-bonding network among several residues within its second-sphere coordination, providing a key structural role towards Mb's functional properties. Our work aims to understand the role of the heme propionates on the...

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Galinato MGI, Trail AM, Steinbeck OR, et al. Influence of heme propionates on the nitrite reductase activity of myoglobin. J Inorg Biochem. 2021;226:111630doi: 10.1016/j.jinorgbio.2021.111630.
Galinato, M. G. I., Trail, A. M., Steinbeck, O. R., Si, Z., Rodland, A. M., & Gowen, J. (2022). Influence of heme propionates on the nitrite reductase activity of myoglobin. Journal of inorganic biochemistry, 226111630. https://doi.org/10.1016/j.jinorgbio.2021.111630
Galinato, Mary Grace I, et al. "Influence of heme propionates on the nitrite reductase activity of myoglobin." Journal of inorganic biochemistry vol. 226 (2022): 111630. doi: https://doi.org/10.1016/j.jinorgbio.2021.111630
Galinato MGI, Trail AM, Steinbeck OR, Si Z, Rodland AM, Gowen J. Influence of heme propionates on the nitrite reductase activity of myoglobin. J Inorg Biochem. 2022 Jan;226:111630. doi: 10.1016/j.jinorgbio.2021.111630. Epub 2021 Oct 16. PMID: 34688205.
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A unified strategy for the stereospecific construction of propionates and acetate-propionates relying on a directed allylic substitution.

Chemistry (Weinheim an der Bergstrasse, Germany)

Reiss T, Breit B.
PMID: 19479928
Chemistry. 2009 Jun 22;15(26):6345-8. doi: 10.1002/chem.200901064.

Flexible friends: A new strategy that relies on o-DPPB-directed allylic substitution has been implemented for the flexible and stereospecific construction of major polyketide and isoprenoid structural elements (see scheme; o-DPPB=ortho-diphenylphosphanyl benzoate; PG=protecting group).

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Reiss T, Breit B. A unified strategy for the stereospecific construction of propionates and acetate-propionates relying on a directed allylic substitution. Chemistry. 2009;15(26):6345-8doi: 10.1002/chem.200901064.
Reiss, T., & Breit, B. (2009). A unified strategy for the stereospecific construction of propionates and acetate-propionates relying on a directed allylic substitution. Chemistry (Weinheim an der Bergstrasse, Germany), 15(26), 6345-8. https://doi.org/10.1002/chem.200901064
Reiss, Tomislav, and Breit, Bernhard. "A unified strategy for the stereospecific construction of propionates and acetate-propionates relying on a directed allylic substitution." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 15,26 (2009): 6345-8. doi: https://doi.org/10.1002/chem.200901064
Reiss T, Breit B. A unified strategy for the stereospecific construction of propionates and acetate-propionates relying on a directed allylic substitution. Chemistry. 2009 Jun 22;15(26):6345-8. doi: 10.1002/chem.200901064. PMID: 19479928.
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Electron Ionization-Induced Release of Coded Isotopic Reporter Ions in an .

Analytical methods : advancing methods and applications

Laulhé S, Geers TE, Shi X, Zhang X, Nantz MH.
PMID: 24235976
Anal Methods. 2013 Sep 21;5(18). doi: 10.1039/C3AY41124A.

We describe an isotope coding strategy that enables simultaneous GC-MS analysis of multiple samples for substrate identification and quantification. The method relies on direct measurement of isotopic ethyl carbenium ions serving as mass spectral tags in a zone of...

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Laulhé S, Geers TE, Shi X, et al. Electron Ionization-Induced Release of Coded Isotopic Reporter Ions in an . Anal Methods. 2013;5(18)doi: 10.1039/C3AY41124A.
Laulhé, S., Geers, T. E., Shi, X., Zhang, X., & Nantz, M. H. (2013). Electron Ionization-Induced Release of Coded Isotopic Reporter Ions in an . Analytical methods : advancing methods and applications, 5(18), . https://doi.org/10.1039/C3AY41124A
Laulhé, Sébastien, et al. "Electron Ionization-Induced Release of Coded Isotopic Reporter Ions in an ." Analytical methods : advancing methods and applications vol. 5,18 (2013). doi: https://doi.org/10.1039/C3AY41124A
Laulhé S, Geers TE, Shi X, Zhang X, Nantz MH. Electron Ionization-Induced Release of Coded Isotopic Reporter Ions in an . Anal Methods. 2013 Sep 21;5(18). doi: 10.1039/C3AY41124A. PMID: 24235976; PMCID: PMC3822575.
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Showing 1 to 12 of 33 entries