Publication

From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds

Elangovan, S., Afanasenko, A., Haupenthal, J., Sun, Z., Liu, Y., Hirsch, A. K. H. & Barta, K., 23-Oct-2019, In : ACS central science. 5, 10, p. 1707-1716 10 p.

Research output: Contribution to journalArticleAcademicpeer-review

APA

Elangovan, S., Afanasenko, A., Haupenthal, J., Sun, Z., Liu, Y., Hirsch, A. K. H., & Barta, K. (2019). From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds. ACS central science, 5(10), 1707-1716. https://doi.org/10.1021/acscentsci.9b00781

Author

Elangovan, Saravanakumar ; Afanasenko, Anastasiia ; Haupenthal, Jörg ; Sun, Zhuohua ; Liu, Yongzhuang ; Hirsch, Anna K H ; Barta, Katalin. / From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps : Modular Synthesis of Biologically Active Lignin-Derived Scaffolds. In: ACS central science. 2019 ; Vol. 5, No. 10. pp. 1707-1716.

Harvard

Elangovan, S, Afanasenko, A, Haupenthal, J, Sun, Z, Liu, Y, Hirsch, AKH & Barta, K 2019, 'From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds', ACS central science, vol. 5, no. 10, pp. 1707-1716. https://doi.org/10.1021/acscentsci.9b00781

Standard

From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps : Modular Synthesis of Biologically Active Lignin-Derived Scaffolds. / Elangovan, Saravanakumar; Afanasenko, Anastasiia; Haupenthal, Jörg; Sun, Zhuohua; Liu, Yongzhuang; Hirsch, Anna K H; Barta, Katalin.

In: ACS central science, Vol. 5, No. 10, 23.10.2019, p. 1707-1716.

Research output: Contribution to journalArticleAcademicpeer-review

Vancouver

Elangovan S, Afanasenko A, Haupenthal J, Sun Z, Liu Y, Hirsch AKH et al. From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds. ACS central science. 2019 Oct 23;5(10):1707-1716. https://doi.org/10.1021/acscentsci.9b00781


BibTeX

@article{b77e2b2e29814ee0869b34a2eeacb1ed,
title = "From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds",
abstract = "Inherently complex, lignin-derived aromatic monomers comprising valuable structural moieties present in many pharmaceuticals would serve as ideal substrates for the construction of biologically active molecules. Here, we describe a strategy that incorporates all intrinsic functional groups present in platform chemicals obtained by lignin depolymerization into value-added amines, using sustainable catalytic methods and benign solvents. Our strikingly efficient protocol provides access to libraries of aminoalkyl-phenol derivatives and seven-membered N-heterocycles directly from wood in two, respectively three, waste-free steps. Several molecules in these libraries have shown promising antibacterial or anticancer activities, emphasizing the advantage of this modular synthetic strategy and the potential for drug discovery. The sustainable catalytic pathways presented here can lead to significant benefits for the pharmaceutical industry where reduction of hazardous waste is a prime concern, and the described strategies that lead to high-value products from non-edible biomass waste streams also markedly increase the economic feasibility of lignocellulosic biorefineries.",
keywords = "PICTET-SPENGLER REACTION, LIGNOCELLULOSE FRACTIONATION, DEPOLYMERIZATION, ACID, BIOSYNTHESIS, VALORIZATION, DERIVATIVES, ANTAGONISTS, CONVERSION, PLATFORM",
author = "Saravanakumar Elangovan and Anastasiia Afanasenko and J{\"o}rg Haupenthal and Zhuohua Sun and Yongzhuang Liu and Hirsch, {Anna K H} and Katalin Barta",
note = "Copyright {\textcopyright} 2019 American Chemical Society.",
year = "2019",
month = oct,
day = "23",
doi = "10.1021/acscentsci.9b00781",
language = "English",
volume = "5",
pages = "1707--1716",
journal = "ACS central science",
issn = "2374-7943",
publisher = "AMER CHEMICAL SOC INC",
number = "10",

}

RIS

TY - JOUR

T1 - From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps

T2 - Modular Synthesis of Biologically Active Lignin-Derived Scaffolds

AU - Elangovan, Saravanakumar

AU - Afanasenko, Anastasiia

AU - Haupenthal, Jörg

AU - Sun, Zhuohua

AU - Liu, Yongzhuang

AU - Hirsch, Anna K H

AU - Barta, Katalin

N1 - Copyright © 2019 American Chemical Society.

PY - 2019/10/23

Y1 - 2019/10/23

N2 - Inherently complex, lignin-derived aromatic monomers comprising valuable structural moieties present in many pharmaceuticals would serve as ideal substrates for the construction of biologically active molecules. Here, we describe a strategy that incorporates all intrinsic functional groups present in platform chemicals obtained by lignin depolymerization into value-added amines, using sustainable catalytic methods and benign solvents. Our strikingly efficient protocol provides access to libraries of aminoalkyl-phenol derivatives and seven-membered N-heterocycles directly from wood in two, respectively three, waste-free steps. Several molecules in these libraries have shown promising antibacterial or anticancer activities, emphasizing the advantage of this modular synthetic strategy and the potential for drug discovery. The sustainable catalytic pathways presented here can lead to significant benefits for the pharmaceutical industry where reduction of hazardous waste is a prime concern, and the described strategies that lead to high-value products from non-edible biomass waste streams also markedly increase the economic feasibility of lignocellulosic biorefineries.

AB - Inherently complex, lignin-derived aromatic monomers comprising valuable structural moieties present in many pharmaceuticals would serve as ideal substrates for the construction of biologically active molecules. Here, we describe a strategy that incorporates all intrinsic functional groups present in platform chemicals obtained by lignin depolymerization into value-added amines, using sustainable catalytic methods and benign solvents. Our strikingly efficient protocol provides access to libraries of aminoalkyl-phenol derivatives and seven-membered N-heterocycles directly from wood in two, respectively three, waste-free steps. Several molecules in these libraries have shown promising antibacterial or anticancer activities, emphasizing the advantage of this modular synthetic strategy and the potential for drug discovery. The sustainable catalytic pathways presented here can lead to significant benefits for the pharmaceutical industry where reduction of hazardous waste is a prime concern, and the described strategies that lead to high-value products from non-edible biomass waste streams also markedly increase the economic feasibility of lignocellulosic biorefineries.

KW - PICTET-SPENGLER REACTION

KW - LIGNOCELLULOSE FRACTIONATION

KW - DEPOLYMERIZATION

KW - ACID

KW - BIOSYNTHESIS

KW - VALORIZATION

KW - DERIVATIVES

KW - ANTAGONISTS

KW - CONVERSION

KW - PLATFORM

U2 - 10.1021/acscentsci.9b00781

DO - 10.1021/acscentsci.9b00781

M3 - Article

C2 - 31660439

VL - 5

SP - 1707

EP - 1716

JO - ACS central science

JF - ACS central science

SN - 2374-7943

IS - 10

ER -

ID: 101015655