DOCSLIB.ORG

Synthesis of Triacetic Acid Lactone Mannich Bases and Their Inhibition of Corrosion John Rey Apostol Romal Iowa State University

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Synthesis of Triacetic Acid Lactone Mannich Bases and Their Inhibition of Corrosion John Rey Apostol Romal Iowa State University Iowa State University Capstones, Theses and Graduate Theses and Dissertations Dissertations 2016 Synthesis of triacetic acid lactone Mannich bases and their inhibition of corrosion John Rey Apostol Romal Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/etd Part of the Chemistry Commons Recommended Citation Romal, John Rey Apostol, "Synthesis of triacetic acid lactone Mannich bases and their inhibition of corrosion" (2016). Graduate Theses and Dissertations. 15802. https://lib.dr.iastate.edu/etd/15802 This Thesis is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Graduate Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. Synthesis of triacetic acid lactone Mannich bases and their inhibition of corrosion by John Rey Apostol Romal A thesis submitted to the graduate faculty in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE Major: Organic Chemistry Program of Study Committee: George A. Kraus, Major Professor Brent Shanks Arthur Winter Iowa State University Ames, Iowa 2016 Copyright © John Rey Apostol Romal, 2016. All rights reserved. ii DEDICATION To my family and friends. iii TABLE OF CONTENTS DEDICATION ........................................................................................................... ii LIST OF ABBREVIATIONS .................................................................................... iv ACKNOWLEDGEMENTS ....................................................................................... vi ABSTRACT………………………………. .............................................................. viii CHAPTER I. MANNICH REACTIONS OF THE BIO-BASED TRIACETIC ACID LACTONE .......................................................................... 1 1.1. Introduction .............................................................................. 1 1.2. Results and Discussion ............................................................ 19 1.3. Conclusion ............................................................................... 33 1.4. Experimental ............................................................................ 33 1.5. References ................................................................................ 45 CHAPTER II. CORROSION INHIBITION OF SMALL ORGANIC MOLECULES AND TRIACETIC ACID LACTONE MANNICH BASES ............................................................................................ 49 2.1. Introduction .............................................................................. 49 2.2. Results and Discussion ............................................................ 63 2.3. Conclusion ............................................................................... 73 2.4. Experimental ............................................................................ 74 2.5. References ................................................................................ 77 CHAPTER III. GENERAL CONCLUSIONS…………………………………….. 80 iv LIST OF ABBREVIATIONS ACAT acyl-CoA cholesterol acyltransferase AcOH acetic acid CDCl3 deuterated chloroform Cu NP copper nanoparticle DCE dichloroethane DHA dehydroacetic acid DMAD dimethylacetylenedicarboxylate DMM dimethoxymethane DMSO dimethylsulfoxide EA ethyl acetate E. Coli Escherichia coli EDG electron-donating group EG ethylene glycol EI electron ionization ESI electronspray ionization EWG electron-withdrawing group FDCA 2,5-furandicarboxylic acid GC gas chromatography HMF 5-hydroxymethylfurfural ICP Inductively Coupled Plasma IE inhibition efficiency v LRMS low resolution mass spectrometry MCR multicomponent reaction MeCN acetonitrile MHz megahertz mM millimolar MS mass spectrometry NMR Nuclear Magnetic Resonance OCV open circuit voltage PEF polyethylene furanoate PEIS Potentiostatic Electron Impedance Spectroscopy PET polyethylene terephthalate ppm parts per million QTOF quadruple time of flight TAL triacetic acid lactone TLC thin-layer chromatography THF tetrahydrofuran UV ultraviolet vi ACKNOWLEDGEMENTS I am grateful for the opportunity of working under the supervision of Dr. George Kraus. There have been many times I feel challenged conducting research in his lab, but with his motivation and passion for mentoring I was able to comprehend. I will always appreciate his patience and understanding. His dedication and excellence in synthetic organic chemistry will always serve as an inspiration. I would like to express my gratitude to my graduate committee members: Dr. Brent Shanks and Dr. Arthur Winter for their time and support throughout my stay in Iowa State University. Their opinions and advices were greatly appreciated. I acknowledge Dr. Wenzhen Li, his student Yang Qiu, and the rest of present Li’s group members for the opportunity to work in the field of electrochemistry. I would also like to recognize Dr. Wenyu Huang and his group for providing me the experience working in the field of catalysis during the first two semesters of my graduate studies. The computational efforts of Logan Fischer and Shinae Kim were also appreciated. I feel delighted working in Kraus lab in the presence of my motivating colleagues: Dr. Uma Wanninayake, Dr. Pengfei Dong, Yang Qu, Ivan Geraskin, and Huangchao Yu. Their motivation and support towards the completion of my Masters of Science study were very much highly appreciated. All the intellectual and personal life discussions will always be cherished. I would especially thank Aaron Zoellner for the great brotherhood he has imparted me. Through my ups and downs in the past year, he has been there to celebrate with and an anchor providing me with great advices and motivation. His unconditional friendship vii will always be treasured. I also want to express my heartfelt appreciation to Dr. Michelle Thompson, Hannah Crotty, and Miles Arthur White for all the motivation, suggestions, and advices they have provided me about research and personal struggles. They have always made themselves available if I need them the most. I am also grateful to Fritzie Rivas, Dr. Kristin Manibog, Mapi Faylon, Katrina Lutap, and Darlene Sanchez for bestowing me with their sisterly-love since I moved in to Ames. The companionship of Eric Schultz, Fitim Kelmendi, Peter Spurgeon, Ming-Hsun Cheng, Charles Nyamekye, and Frank Hanes were also greatly acknowledged. Finally, I would want to express my heartfelt thanks and dedication of this success to my parents Joy and Rey Romal for their sacrifices and unconditional love they have given me my entire life. They have not only provided me with the necessities of life, but they also have endowed me with the luxury of it. They have nurtured me to be resilient, hardworking, and patient. I would also want to dedicate this work to my extended family that have always shown me their love and support towards my graduate studies. viii ABSTRACT Our society has relied mostly on fossil-based materials as source of carbon for industrially important chemicals. The non-renewability of this petroleum-based material, however, requires an alternative for sustainability. Presently, there has already been great advancement in utilizing biomass as a renewable carbon source. Triacetic acid lactone (TAL) has been explored as a potential renewable platform chemical by the Center for Biorenewable Chemicals (CBiRC). In the presence of microbial and enzymatic biocatalysts, TAL can be biosynthesized from glucose. Subsequently, TAL can be transformed to variety of high-valued commodity chemicals using chemical catalysts. In Chapter 1 of this work, an efficient method was developed to utilize TAL in the 3-components Mannich reaction. This multi-component reaction is an efficient way of making highly-functionalized molecules. The participation of TAL as the enolizable component in the Mannich reaction has not been well studied in the literature. The successful production of Mannich bases containing TAL moiety demonstrates the versatility of TAL as a platform chemical. In Chapter 2, the corrosion inhibition activity of 2-pyrones, pyridines, and TAL- derived Mannich bases in mild steel was evaluated. There already exist organic molecules corrosion inhibitors. Some TAL-based molecules and pyridines, however, have not been very well known for this application. This chapter gives an overview of other potential small organic molecule corrosion inhibitors. Structure similarity with the previously studied, opuntiol, is the basis for evaluating the efficiency of these molecules. Further studies are still needed to compare the activity of these organic molecules with the corrosion inhibitors used in the industry. ix ~ To God be the glory ~ 1 CHAPTER I MANNICH REACTIONS OF THE BIO-BASED TRIACETIC ACID LACTONE 1.1 Introduction 1.1.1 Progress to bio-based platform chemicals Presently, numerous industries from plastics, textiles, and cosmetics, to polymers, pharmaceuticals, and fuel rely on petroleum-based chemicals as one of the raw materials for production. The gradual depletion of fossil-based resources poses a concern to these chemical industries. In addition to this, the risk in coal mining and the generation of environmentally harmful by-products are also factors to seek an alternative for the production of energy. As a result, several efforts have been made to resolve this issue. Many believe that the most feasible solution is
Load more

Recommended publications
  • Study of Reactions of Two Mannich Bases Derived of 4’-Hydroxychalcones with Glutathione by RP‑TLC, RP‑HPLC and RP‑HPLC‑ESI‑MS Analysis
    http://dx.doi.org/10.21577/0103-5053.20160260 J. Braz. Chem. Soc., Vol. 28, No. 6, 1048-1062, 2017. Printed in Brazil - ©2017 Sociedade Brasileira de Química 0103 - 5053 $6.00+0.00 Article Study of Reactions of Two Mannich Bases Derived of 4’-Hydroxychalcones with Glutathione by RP-TLC, RP-HPLC and RP-HPLC-ESI-MS Analysis Aline Bernardes,a,b Caridad N. Pérez,a Mátyás Mayer,c Cameron C. da Silva,a Felipe T. Martinsa and Pál Perjési*,b aInstituto de Química, Universidade Federal de Goiás, 74690-900 Goiânia-GO, Brazil bInstitute of Pharmaceutical Chemistry and cDepartment of Forensic Medicine, University of Pécs, H-7624 Pécs, Hungary 4’-Hydroxychalcones have been reported to possess several beneficial biological effects. Several lines of evidence accumulated to demonstrate increased biological activities of the Mannich base derivatives of the parent 4’-hydroxychalcones. Bioactivities of chalcones and related α,β-unsaturated ketones are frequently associated with their reactivity with cellular thiols, such as GSH. For comparison of GSH reactivity, two bis Mannich bases of two 4’-hydroxychalcones were synthesized and reacted with GSH under non-cellular conditions. Reversed-phase thin layer chromatography (RP-TLC) and reversed-phase high performance liquid chromatography (RP-HPLC) analysis showed formation of two polar products which structures were confirmed by RP-HPLC-ESI-MS (RP-HPLC-electrospray ionization mass spectrometry) as 1:1 chalcone-GSH adducts in each case. At pH values below 8.0, the two bis Mannich bases showed higher GSH reactivity than two 4’-hydroxychalcones. Influence of the nature of the amino groups, the ring-B substituents and pH of the medium on reactivity was also investigated.
    [Show full text]
  • Rewiring Yarrowia Lipolytica Toward Triacetic Acid Lactone for Materials Generation
    Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation Kelly A. Markhama,1, Claire M. Palmerb,1, Malgorzata Chwatkoa, James M. Wagnera, Clare Murraya, Sofia Vazqueza, Arvind Swaminathana, Ishani Chakravartya, Nathaniel A. Lynda, and Hal S. Alpera,b,2 aMcKetta Department of Chemical Engineering, The University of Texas at Austin, Austin, TX 78712; and bInstitute for Cellular and Molecular Biology, The University of Texas at Austin, Austin, TX 78712 Edited by Sang Yup Lee, Korea Advanced Institute of Science and Technology, Daejeon, Republic of Korea, and approved January 22, 2018 (received for review December 6, 2017) Polyketides represent an extremely diverse class of secondary me- or challenging syntheses, this is not an option for any larger-scale tabolites often explored for their bioactive traits. These molecules are chemistry application. also attractive building blocks for chemical catalysis and polymeriza- Here, we focus on the interesting, yet simple, polyketide, tri- tion. However, the use of polyketides in larger scale chemistry acetic acid lactone (TAL) as it is derived from two common applications is stymied by limited titers and yields from both microbial polyketide precursors, acetyl–CoA and malonyl–CoA. TAL has and chemical production. Here, we demonstrate that an oleaginous been demonstrated as a platform chemical that can be converted organism (specifically, Yarrowia lipolytica) can overcome such produc- into a variety of valuable products traditionally derived from tion limitations owing to a natural propensity for high flux through fossil fuels including sorbic acid, a common food preservative acetyl–CoA. By exploring three distinct metabolic engineering strate- with a global demand of 100,000 t (1, 15–18).
    [Show full text]
  • Generation of a Structurally Diverse Library Through Alkylation and Ring
    70 Acta Chim. Slov. 2013, 60, 70–80 Scientific paper Generation of a Structurally Diverse Library through Alkylation and Ring Closure Reactions Using 3-Dimethylamino-1-(thiophen-2-yl)propan-1-one Hydrochloride* Gheorghe Roman Petru Poni Institute of Macromolecular Chemistry, 41A Aleea Gr. Ghica Vodâ, Ias¸i 700487, Romania Corresponding author: E-mail: [email protected] Received: 01-06-2012 Abstract 3-Dimethylamino-1-(thiophen-2-yl)propan-1-one hydrochloride (2), a ketonic Mannich base derived from 2-acetyl- thiophene, was used as a starting material in different types of alkylation and ring closure reactions with a view to gene- rate a structurally diverse library of compounds. Compound 2 reacts with S-alkylated dithiocarbamic acid salts and aryl mercaptans to produce dithiocarbamates and thioethers, respectively. The dimethylamino moiety in compound 2 was exchanged with various aliphatic secondary and aromatic primary and secondary amines, whereas monocyclic NH-azoles such as pyrazole, imidazole, 1,2,4-triazole, and tetrazole were N-alkylated by compound 2. Ketones, pyrrole and in- doles have been the substrates subjected to C-alkylation reactions by compound 2. Ring closure reactions of compound 2 with a suitable bifunctional nucleophile yielded pyrazolines, pyridines, 2,3-dihydro-1,5-1H-benzodiazepines, 2,3- dihydro-1,5-1H-benzothiazepine, pyrimido[1,2-a]benzimidazole and 4-hydroxypiperidine derivatives. Keywords: Ketonic Mannich base, alkylation, amine exchange, cyclization. 1. Introduction through the replacement of the easily leaving dimethyla- mino group by various nucleophiles. Also, several cycliza- The chemistry of Mannich bases has drawn a great tions of the aforementioned Mannich base with bifunctio- deal of attention owing to the high synthetic potential and nal nucleophiles to 5-, 6- and 7-membered nitrogen-con- the outstanding applications of this class of compounds.2–4 taining heterocycles have been investigated.
    [Show full text]
  • Engineering Acetyl-Coa Metabolic Shortcut for Eco-Friendly Production
    bioRxiv preprint doi: https://doi.org/10.1101/614131; this version posted April 19, 2019. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. 1 2 3 4 Engineering acetyl-CoA metabolic shortcut for eco-friendly 5 production of polyketides triacetic acid lactone in Yarrowia lipolytica 6 7 8 Huan Liu1,2, Monireh Marsafari 1, 3, Fang Wang2, Li Deng2,* and Peng Xu1,* 9 10 11 1Department of Chemical, Biochemical and Environmental Engineering, University of 12 Maryland, Baltimore County, Baltimore, MD 21250. 13 14 2College of Life Science and Technology, Beijing University of Chemical 15 Technology, Beijing, China. 16 17 3Department of Agronomy and Plant Breeding, University of Guilan, Rasht, Islamic 18 Republic of Iran 19 20 21 22 23 24 25 26 27 28 * Corresponding author Tel: +1(410)-455-2474; fax: +1(410)-455-1049. E-mail address: [email protected] (PX) and [email protected] (LD). 1 bioRxiv preprint doi: https://doi.org/10.1101/614131; this version posted April 19, 2019. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. 29 Abstract 30 Acetyl-CoA is the central metabolic node connecting glycolysis, Krebs cycle and 31 fatty acids synthase. Plant-derived polyketides, are assembled from acetyl-CoA and 32 malonyl-CoA, represent a large family of biological compounds with diversified 33 bioactivity. Harnessing microbial bioconversion is considered as a feasible approach 34 to large-scale production of polyketides from renewable feedstocks.
    [Show full text]
  • Mannich Reaction
    1. Introduction 1.1- Mannich Reaction The Mannich reaction is three component condensation in which a compound containing an active hydrogen atom is allowed to react with formaldehyde and an NH-amine derivative . Secondary amines rather than primary amines and ammonia are employed , the resulting product (Mannich Base ) is an amine compound having the N atom linked to the R substrate through a methylene group 1,2. The aminoalkylation of CH-acidic compounds was described by several authors as early as the 19th. century. However, it was Carl Mannich who was the first to recognize the enormous significance of this reaction , and it was he who extended the chemistry into a broad based synthetic methodology through systematic research. Since then this reaction that now carries his name has developed into one of the most important C-C bond-forming reactions in organic chemistry3,4. The Mannich reaction is a classical method for the preparation of β -aminoketones and aldehydes (Mannich bases) and, as such, is one of the most important basic reaction types in organic chemistry. It is the key step in the synthesis of numerous pharmaceuticals and natural products3,4. 1 The Mannich reaction can be presented by the following equation: The essential feature of the reaction is the replacement of the active hydrogen atom by an aminomethyl or substituted aminomethyl group. The symbolizes the active hydrogen component which includes ketones, aldehydes, acids, esters, phenols, acetylenes, picolines, nitroalkanes and quinolines1,2. 1.2- Mechanism of the Mannich reaction The mechanism of the Mannich reaction has been well investigated, the condensation reaction occurs in two steps: first, the amine reacts with formaldehyde to give condensation product (5 ), (6), ( 7) (step I) which then attacks the substrate R-H (step II) .The reaction does not normally follow the other possible route (step III and IV) ; however, some successful reaction between hydroxymethyl derivatives (8) and alkylamines to give Mannich bases (9) should be mentioned .
    [Show full text]
  • Synthesis and Characterization of Some Novel Mannich Base Compounds
    Synthesis and Characterization of Some Novel Mannich Base Compounds Dr. P. Sounthari Dr. P. R. Sivakumar Dr. P. Sounthari Dr. P.R. Sivakumar Assistant Professor, PG & Research Department of Department of Chemistry, Chemistry, PSG College of Arts and Government Arts Science, Coimbatore- College (Autonomous), 641 014. Coimbatore - 641 018, Tamil Nadu, India. ISBN 978-93-89631-02-9 ISBN 978-93-89631-04-3 (eBook) https://doi.org/10.34256/ioriip196 © IOR INTERNATIONAL PRESS. This book is an open access publication. Open Access This book is licensed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license and indicate if changes were made. The images or other third party material in this book are included in the book’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the book’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication.
    [Show full text]
  • The Biochemistry of Certain Fungicides in the Animal Body
    THE BIOCHEMISTRY OF CERTAIN FUNGICIDES IN THE ANIMAL BODY By THOMAS EDWARD BARMAN A Theists presented in accordance with the regulations governing the award of the degree of Doctor of Philosophy in the University of London. partment of Biochemistry, St. Mary is Hospital Medical.School, Idomdon, W.2, August, 1961. TO iii ABSTRACT OF THESIS The fates of dehydroacetic acid and of two closely related pyronee, triacetic acid lactone and imino dehydroacetic acid have been investig- ated in the rabbit and rat. The synthesis of (14Cid-dehydroacetic acid* 'from 14C.1-acetyl bromide is described; in addition, the preparation of (14031-triacetic acid lactone and [ 4O4)-imino dehydroacetic acid, both from [140 J-dehydroacetic acid, are reported. By administering these labelled compounds to rabbits and rats, it was shown that [2.40J-dehydro- acetic acid gave rise to about 10% 14002 in the expired air, (1403). triacetio acid lactone to 50% and Cihed-imino dehydroacetic acid to 2..3%. In the urines of animals dosed with PICJ-dehydroacetic acid, dehydroacetic acid itself, hydroxy-dehydroacetic acid, their respective imino derivatives, triacetic acid lactone, urea and two metabolites of. unknown structures, metabolites "X" and lin were shown to be present by colour chromatography and eutoradiography. Of these, dehydroacetic acid, its hydrozy derivative and metabolitelfiXo'have been iao1ated, and imino - dehydroacetic acid and imino'hydroxydehydroacetic acid shown to be urinary artifacts. Work done on rat liver and kidney slices has established that, while triacetic acid lactone was oxidised in both, dehydroacetic acid was only attacked to a detectable extent,in liver slices. The binding of dehydroacetic acid to plasma albumin was shown by paper electro- phoresis.
    [Show full text]
  • Rewiring Yarrowia Lipolytica Toward Triacetic Acid Lactone for Materials Generation
    Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation Kelly A. Markhama,1, Claire M. Palmerb,1, Malgorzata Chwatkoa, James M. Wagnera, Clare Murraya, Sofia Vazqueza, Arvind Swaminathana, Ishani Chakravartya, Nathaniel A. Lynda, and Hal S. Alpera,b,2 aMcKetta Department of Chemical Engineering, The University of Texas at Austin, Austin, TX 78712; and bInstitute for Cellular and Molecular Biology, The University of Texas at Austin, Austin, TX 78712 Edited by Sang Yup Lee, Korea Advanced Institute of Science and Technology, Daejeon, Republic of Korea, and approved January 22, 2018 (received for review December 6, 2017) Polyketides represent an extremely diverse class of secondary me- or challenging syntheses, this is not an option for any larger-scale tabolites often explored for their bioactive traits. These molecules are chemistry application. also attractive building blocks for chemical catalysis and polymeriza- Here, we focus on the interesting, yet simple, polyketide, tri- tion. However, the use of polyketides in larger scale chemistry acetic acid lactone (TAL) as it is derived from two common applications is stymied by limited titers and yields from both microbial polyketide precursors, acetyl–CoA and malonyl–CoA. TAL has and chemical production. Here, we demonstrate that an oleaginous been demonstrated as a platform chemical that can be converted organism (specifically, Yarrowia lipolytica) can overcome such produc- into a variety of valuable products traditionally derived from tion limitations owing to a natural propensity for high flux through fossil fuels including sorbic acid, a common food preservative acetyl–CoA. By exploring three distinct metabolic engineering strate- with a global demand of 100,000 t (1, 15–18).
    [Show full text]
  • MARKHAM-DISSERTATION-2018.Pdf
    Copyright by Kelly Ann Markham 2018 The Dissertation Committee for Kelly Ann Markham Certifies that this is the approved version of the following dissertation: Expanding the Product Portfolio of Yarrowia lipolytica through Metabolic Engineering and Synthetic Biology Tool Development Committee: Hal Alper, Supervisor Lydia Contreras George Georgiou Adrian Keatinge-Clay Expanding the Product Portfolio of Yarrowia lipolytica through Metabolic Engineering and Synthetic Biology Tool Development by Kelly Ann Markham Dissertation Presented to the Faculty of the Graduate School of The University of Texas at Austin in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy The University of Texas at Austin August 2018 Dedication For those who have been made to feel small. You are strong. You are important. You deserve to take up space. Acknowledgements First and foremost, I want to thank Dr. Hal Alper for being a supportive advisor and helping me grow in all aspects of being a scientist. From helpful tricks for personal development like working with Microsoft (that alignment function will always haunt me) to high expectations requiring proper experimental design, I have learned an amazing amount from Hal in the last five years. Hal has proven willing to take time to make sure that students are taken care of and meeting their full potential. Thanks for taking that time to make us all better researchers and giving us room to explore different projects and ideas. I am forever grateful for the opportunity to work with Hal and the Alper lab. Next, I would like to thank Dr. Lydia Contreras, Dr. George Georgiou, and Dr.
    [Show full text]
  • Bioengineering Triacetic Acid Lactone Production in Yarrowia Lipolytica for Pogostone Synthesis
    Downloaded from orbit.dtu.dk on: Oct 01, 2021 Bioengineering triacetic acid lactone production in Yarrowia lipolytica for pogostone synthesis Yu, James; Landberg, Jenny Marie; Shavarebi, Farbod; Bilanchone, Virginia; Okerlund, Adam; Wanninayake, Umayangani; Zhao, Le; Kraus, George; Sandmeyer, Suzanne Published in: Biotechnology and Bioengineering Link to article, DOI: 10.1002/bit.26733 Publication date: 2018 Document Version Peer reviewed version Link back to DTU Orbit Citation (APA): Yu, J., Landberg, J. M., Shavarebi, F., Bilanchone, V., Okerlund, A., Wanninayake, U., Zhao, L., Kraus, G., & Sandmeyer, S. (2018). Bioengineering triacetic acid lactone production in Yarrowia lipolytica for pogostone synthesis. Biotechnology and Bioengineering, 115(9), 2383-2388. https://doi.org/10.1002/bit.26733 General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. Users may download and print one copy of any publication from the public portal for the purpose of private study or research. You may not further distribute the material or use it for any profit-making activity or commercial gain You may freely distribute the URL identifying the publication in the public portal If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. HHS Public Access Author manuscript Author ManuscriptAuthor Manuscript Author Biotechnol Manuscript Author Bioeng. Author Manuscript Author manuscript; available in PMC 2019 November 14.
    [Show full text]
  • Selective C-O Hydrogenolysis and Decarboxylation of Biomass-Derived Heterocyclic Compounds Over Heterogeneous Catalysts
    Selective C-O Hydrogenolysis and Decarboxylation of Biomass-Derived Heterocyclic Compounds over Heterogeneous Catalysts By Mei Chia A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy (Chemical Engineering) At the UNIVERSITY OF WISCONSIN-MADISON 2013 Date of final oral examination: 11th July 2013 The dissertation is approved by the following members of the Final Oral Committee: James A. Dumesic, Professor, Chemical and Biological Engineering Thomas F. Kuech, Professor, Chemical and Biological Engineering Manos Mavrikakis, Professor, Chemical and Biological Engineering Brian F. Pfleger, Assistant Professor, Chemical and Biological Engineering Dane Morgan, Associate Professor, Materials Science and Engineering i Selective C-O Hydrogenolysis and Decarboxylation of Biomass-Derived Heterocyclic Compounds over Heterogeneous Catalysts Mei Chia Under the supervision of Professor James A. Dumesic At the University of Wisconsin-Madison The catalytic deoxygenation of biomass-derived compounds through selective C-O hydrogenolysis, catalytic transfer hydrogenation and lactonization, and decarboxylation to value- added chemicals over heterogeneous catalysts was examined under liquid phase reaction conditions. The reactions studied involve the conversion or production of heterocyclic compounds, specifically, cyclic ethers, lactones, and 2-pyrones. A bimetallic RhRe/C catalyst was found to be selective for the hydrogenolysis of secondary C-O bonds for a broad range cyclic ethers and polyols. Results
    [Show full text]
  • Mannich Base-Connected Syntheses Mediated by Ortho-Quinone Methides
    Mannich base-connected syntheses mediated by ortho-quinone methides Petra Barta, Ferenc Fülöp and István Szatmári* Review Open Access Address: Beilstein J. Org. Chem. 2018, 14, 560–575. Institute of Pharmaceutical Chemistry and Research Group for doi:10.3762/bjoc.14.43 Stereochemistry, Hungarian Academy of Sciences, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary Received: 06 November 2017 Accepted: 10 February 2018 Email: Published: 06 March 2018 István Szatmári* - [email protected] Associate Editor: J. A. Murphy * Corresponding author © 2018 Barta et al.; licensee Beilstein-Institut. Keywords: License and terms: see end of document. aminophenols; [4 + 2] cycloaddition; dienophile; Mannich reaction; ortho-quinone methide Abstract This article provides an overview about specifically modified Mannich reactions where the process involves an ortho-quinone methide (o-QM) intermediate. The reactions are classified on the basis of the o-QM source followed by the reactant, e.g., the dieno- phile partner in cycloaddition reactions (C=C or C=N dienophiles) or by the formation of multicomponent Mannich adducts. Due to the important pharmacological activities of these reactive o-QM intermediates, special attention is paid to the biological activity of these compounds. Review Introduction The Mannich reaction is an important, one-pot, multicompo- benzaldehyde and 2-naphthol. This protocol is known as Betti nent, C–C bond forming reaction that is widely used in the syn- reaction and the compound formed as Betti base [7-9]. Several theses of many biologically active and natural compounds [1-5]. examples have been published to extend the reaction and to Originally, the Mannich product is formed through a three-com- synthesize varied substituted aminonaphthol derivatives [10].
    [Show full text]