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Heinks, T., Merz, L. M., Liedtke, J., Hoehne, M., van Langen, L. M., Bornscheuer, U. T., . . . Berglund, P. (2023). Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases. Catalysts, 13(5), 875, Article ID 875.
Open this publication in new window or tab >>Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases
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2023 (English)In: Catalysts, E-ISSN 2073-4344, Vol. 13, no 5, p. 875-, article id 875Article in journal (Refereed) Published
Abstract [en]

Building blocks with amine functionality are crucial in the chemical industry. Biocatalytic syntheses and chemicals derived from renewable resources are increasingly desired to achieve sustainable production of these amines. As a result, renewable materials such as furfurals, especially furfurylamines like 5-(hydroxymethyl)furfurylamine (HMFA) and 2,5-di(aminomethyl)furan (DAF), are gaining increasing attention. In this study, we identified four different amine transaminases (ATAs) that catalyze the reductive amination of 5-(hydroxymethyl)furfural (HMF) and 2,5-diformylfuran (DFF). We successfully immobilized these ATAs on glutaraldehyde-functionalized amine beads using multiple binding and on amine beads by site-selective binding of the unique Ca-formylglycine within an aldehyde tag. All immobilized ATAs were efficiently reused in five repetitive cycles of reductive amination of HMF with alanine as co-substrate, while the ATA from Silicibacter pomeroyi (ATA-Spo) also exhibited high stability for reuse when isopropylamine was used as an amine donor. Additionally, immobilized ATA-Spo yielded high conversion in the batch syntheses of HMFA and DAF using alanine (87% and 87%, respectively) or isopropylamine (99% and 98%, respectively) as amine donors. We further demonstrated that ATA-Spo was effective for the reductive amination of HMF with alanine or isopropylamine in continuous-flow catalysis with high conversion up to 12 days (48% and 41%, respectively).

Place, publisher, year, edition, pages
MDPI AG, 2023
Keywords
amine transaminase, biocatalysis, DFF, flow synthesis, HMF, immobilization, isopropylamine, reuse stability
National Category
Biochemistry and Molecular Biology
Identifiers
urn:nbn:se:kth:diva-329463 (URN)10.3390/catal13050875 (DOI)000997683600001 ()2-s2.0-85160787938 (Scopus ID)
Note

QC 20230621

Available from: 2023-06-21 Created: 2023-06-21 Last updated: 2023-06-26Bibliographically approved
Sheludko, Y. V., Slagman, S., Gittings, S., Charnock, S. J., Land, H., Berglund, P. & Fessner, W. (2022). Enantioselective Synthesis of Pharmaceutically Relevant Bulky Arylbutylamines Using Engineered Transaminases. Advanced Synthesis and Catalysis, 364(17), 2972-2981
Open this publication in new window or tab >>Enantioselective Synthesis of Pharmaceutically Relevant Bulky Arylbutylamines Using Engineered Transaminases
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2022 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 364, no 17, p. 2972-2981Article in journal (Refereed) Published
Abstract [en]

ATAs engineered for having an enlarged small binding pocket were applied for the synthesis of enantiomerically pure (R)-benzo[1,3]dioxol-5-yl-butylamine, a chiral component of human leukocyte elastase inhibitor DMP 777 (L-694,458). Kinetic resolution of the racemic amine was performed by using the L59A variant of the (S)-selective ATA from Chromobacterium violaceum (Cv-ATA), providing the residual (R)-enantiomer in excellent yield and >99% ee. At moderate enzyme loading and absence of co-solvent, high volumetric productivity of 0.22 mol L−1 h−1 (42.5 g L−1 h−1) was achieved. Complementarily, the (S)-enantiomer was generated via kinetic resolution using the (R)-selective ATA-117-Rd11 from Arthrobacter sp. with acetone as the amino acceptor. In an alternative approach, we employed ATA-117-Rd11 for the asymmetric amination of the prochiral ketone precursor, which at 86% conversion gave the (R)-benzo[1,3]dioxol-5-yl-butylamine with excellent >99% ee. We further evaluated the utility of Cv-ATA L59A for the asymmetric synthesis of pharmaceutically relevant (S)-1-phenylbutan-1-amine, a chiral component of the deubiquitinase inhibitor degrasyn (WP1130). The enzyme showed good tolerance to high concentrations of isopropylamine, producing (S)-1-phenylbutan-1-amine in enantiomerically pure form (>99% ee).

Place, publisher, year, edition, pages
John Wiley & Sons, 2022
Keywords
aminotransferase, biocatalysis, chiral amines, kinetic resolution, protein engineering
National Category
Organic Chemistry
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-316345 (URN)10.1002/adsc.202200403 (DOI)000850276600012 ()2-s2.0-85134383982 (Scopus ID)
Note

QC 20220926

Available from: 2022-08-15 Created: 2022-08-15 Last updated: 2024-03-15Bibliographically approved
Högfeldt, A.-K., Gumaelius, L., Berglund, P., Kari, L., Pears, A. & Kann, V. (2022). Leadership, support and organisation for academics'€™ participation in engineering education change for sustainable development. European Journal of Engineering Education
Open this publication in new window or tab >>Leadership, support and organisation for academics'€™ participation in engineering education change for sustainable development
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2022 (English)In: European Journal of Engineering Education, ISSN 0304-3797, E-ISSN 1469-5898Article in journal (Refereed) Published
Abstract [en]

This work spotlights the experiences from ten years of implementing sustainable development in all educational programs at a technical university. With a focus on the critical issue of involving more academics in the work, experiences are shared through an ethnographic account including focus group interviews. "€˜Sustainable development"€™ has been perceived as both superficial and overwhelming; unclear yet somehow predetermined; it has been perceived to demand non-existent space in the curriculum; and it has challenged the academics regardless of the subjects'€™ relatedness to sustainability. It is concluded that the evolution of a web of interconnected people, key academics, activities, norms and tools has contributed to an increased participation. The work for authenticity, reliability and feasibility, along with institution-wide and long-term academic development tools is presented.

Place, publisher, year, edition, pages
Informa UK Limited, 2022
Keywords
Academic leadership, academic development, activity theory, social practice theory, participatory practices
National Category
Learning
Research subject
Education and Communication in the Technological Sciences
Identifiers
urn:nbn:se:kth:diva-317220 (URN)10.1080/03043797.2022.2106824 (DOI)000836131500001 ()2-s2.0-85135264799 (Scopus ID)
Note

QC 20220913

Available from: 2022-09-07 Created: 2022-09-07 Last updated: 2022-09-13Bibliographically approved
Kretschmer, M., Ceña-Diez, R., Butnarasu, C., Silveira, V., Dobryden, I., Visentin, S., . . . Yan, H. (2022). Synthetic Mucin Gels with Self-Healing Properties Augment Lubricity and Inhibit HIV-1 and HSV-2 Transmission. Advanced Science, 9(32), 2203898
Open this publication in new window or tab >>Synthetic Mucin Gels with Self-Healing Properties Augment Lubricity and Inhibit HIV-1 and HSV-2 Transmission
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2022 (English)In: Advanced Science, ISSN 2198-3844, Vol. 9, no 32, p. 2203898-Article in journal (Refereed) Published
Abstract [en]

Mucus is a self-healing gel that lubricates the moist epithelium and provides protection against viruses by binding to viruses smaller than the gel’s mesh size and removing them from the mucosal surface by active mucus turnover. As the primary nonaqueous components of mucus (≈0.2%–5%, wt/v), mucins are critical to this function because the dense arrangement of mucin glycans allows multivalence of binding. Following nature’s example, bovine submaxillary mucins (BSMs) are assembled into “mucus-like” gels (5%, wt/v) by dynamic covalent crosslinking reactions. The gels exhibit transient liquefaction under high shear strain and immediate self-healing behavior. This study shows that these material properties are essential to provide lubricity. The gels efficiently reduce human immunodeficiency virus type 1 (HIV-1) and genital herpes virus type 2 (HSV-2) infectivity for various types of cells. In contrast, simple mucin solutions, which lack the structural makeup, inhibit HIV-1 significantly less and do not inhibit HSV-2. Mechanistically, the prophylaxis of HIV-1 infection by BSM gels is found to be that the gels trap HIV-1 by binding to the envelope glycoprotein gp120 and suppress cytokine production during viral exposure. Therefore, the authors believe the gels are promising for further development as personal lubricants that can limit viral transmission.

Place, publisher, year, edition, pages
Wiley, 2022
Keywords
HIV-1, HSV-2, immune suppression, lubricant, mucin hydrogels, self-healing, strain-weakening, Crosslinking, Diseases, Gels, Hydrogels, Mammals, Self-healing materials, Shear strain, Sols, Herpes virus type 2, Human immunodeficiency virus, Human immunodeficiency virus type 1, Mesh size, Mucin hydrogel, Mucosal surface, Self-healing properties, Viruses
National Category
Microbiology in the medical area
Identifiers
urn:nbn:se:kth:diva-322514 (URN)10.1002/advs.202203898 (DOI)000853580200001 ()36104216 (PubMedID)2-s2.0-85137917305 (Scopus ID)
Note

QC 20221216

Available from: 2022-12-16 Created: 2022-12-16 Last updated: 2022-12-19Bibliographically approved
Merz, L. M., van Langen, L. M. & Berglund, P. (2022). The Role of Buffer, Pyridoxal 5'-phosphate and Light on the Stability of the Silicibacter Pomeroyi Transaminase. ChemCatChem, n/a(n/a)
Open this publication in new window or tab >>The Role of Buffer, Pyridoxal 5'-phosphate and Light on the Stability of the Silicibacter Pomeroyi Transaminase
2022 (English)In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. n/a, no n/aArticle in journal (Refereed) Published
Abstract [en]

Transaminases are pyridoxal 5’-phosphate (PLP)-dependent enzymes that transfer amino-functions. The transaminase from Silicibacter pomeroyi (SpATA) exhibits a broad substrate spectrum. In this work we examined the effect of different conditions (light, buffer and PLP-concentration) on the stability of SpATA, as well as the causes for these effects. The enzyme was stored either in TRIS or CHES with 0–10 mM added PLP at 22 °C. The samples were either kept dark or they were exposed to light. The results show that invariably, all samples kept in darkness exhibited longer half-life times than the ones exposed to light. An increase in the half-life from 8 h to 720 h could be achieved solely by keeping the sample dark. Especially samples in CHES buffer inactivated faster in light the more PLP was present, due to the degradation of PLP. In TRIS however, an imine-bond between TRIS and PLP protects PLP from degradation.

Place, publisher, year, edition, pages
Wiley, 2022
Keywords
amine transaminase, enzyme stability, pyridoxal-5'-phosphate, biocatalysis, light inactivation
National Category
Biochemistry and Molecular Biology Biocatalysis and Enzyme Technology
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-322508 (URN)10.1002/cctc.202201174 (DOI)000894188100001 ()2-s2.0-85143484334 (Scopus ID)
Projects
Horizon 2020 MSCA INTERfaces
Funder
EU, Horizon 2020, 860414
Note

QC 20221221

Available from: 2022-12-16 Created: 2022-12-16 Last updated: 2022-12-21Bibliographically approved
Högfeldt, A.-K., Kann, V., Berglund, P., Kari, L., Gumaelius, L. & Pears, A. (2021). Organizing for Capacity and Involvement among Faculty, Students and Staff in Engineering Education Change: 10 Years of Development. In: Proceedings of 2021 World Engineering Education Forum/Global Engineering Deans Council, WEEF/GEDC 2021: . Paper presented at 2021 World Engineering Education Forum/Global Engineering Deans Council, WEEF/GEDC 2021, Madrid, Spain, 15-18 November 2021 (pp. 340-348). Institute of Electrical and Electronics Engineers Inc.
Open this publication in new window or tab >>Organizing for Capacity and Involvement among Faculty, Students and Staff in Engineering Education Change: 10 Years of Development
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2021 (English)In: Proceedings of 2021 World Engineering Education Forum/Global Engineering Deans Council, WEEF/GEDC 2021, Institute of Electrical and Electronics Engineers Inc. , 2021, p. 340-348Conference paper, Published paper (Refereed)
Abstract [en]

KTH, as most universities, is going through major transformations to respond to the challenges in society. In this contribution, we present ten years of development work that has aimed to enable strengthened participation in educational change, across KTH's organizational boundaries-among teachers, students, and administrative staff. A practitioner and action-oriented approach has guided the development work, from 2011 to today, in creating new meeting arenas. The pandemic outbreak and the associated paralysis of our normal activities proved to lead to an increased importance of the established arenas for educational issues. A broadening could be seen in participating actors and a significant increase in the number of participants. We conclude with emphasizing the value we see with organizing for participation in the transformation of higher education. 

Place, publisher, year, edition, pages
Institute of Electrical and Electronics Engineers Inc., 2021
Keywords
capacity building, communities of practice, future education, organization, participation, Engineering education, Action-oriented, Administrative staff, Education changes, Organizational boundaries, Student staff, Teachers', Students
National Category
Learning
Identifiers
urn:nbn:se:kth:diva-316360 (URN)10.1109/WEEF/GEDC53299.2021.9657461 (DOI)2-s2.0-85124793705 (Scopus ID)
Conference
2021 World Engineering Education Forum/Global Engineering Deans Council, WEEF/GEDC 2021, Madrid, Spain, 15-18 November 2021
Note

Part of proceedings: ISBN 978-1-6654-2488-2

QC 20220816

Available from: 2022-08-16 Created: 2022-08-16 Last updated: 2022-08-16Bibliographically approved
Högfeldt, A.-K., Kann, V., Berglund, P., Kari, L., Gumaelius, L. & Pears, A. (2021). Organizing for Capacity and Involvement Among Faculty, Students and Staff in Fingineering Education Change-10 Years of Development. In: 2021 WORLD ENGINEERING EDUCATION FORUM/GLOBAL ENGINEERING DEANS COUNCIL (WEEF/GEDC): . Paper presented at World Engineering Education Forum (WEEF) / Global-Engineering-Deans-Council (GEDC) Conference, NOV 15-18, 2021, Madrid, SPAIN (pp. 340-348). IEEE
Open this publication in new window or tab >>Organizing for Capacity and Involvement Among Faculty, Students and Staff in Fingineering Education Change-10 Years of Development
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2021 (English)In: 2021 WORLD ENGINEERING EDUCATION FORUM/GLOBAL ENGINEERING DEANS COUNCIL (WEEF/GEDC), IEEE , 2021, p. 340-348Conference paper, Published paper (Refereed)
Abstract [en]

KTH, as most universities, is going through major transformations to respond to the challenges in society. In this contribution, we present ten years of development work that has aimed to enable strengthened participation in educational change, across KTH's organizational boundaries - among teachers, students, and administrative staff. A practitioner and action-oriented approach has guided the development work, from 2011 to today, in creating new meeting arenas. The pandemic outbreak and the associated paralysis of our normal activities proved to lead to an increased importance of the established arenas for educational issues. A broadening could be seen in participating actors and a significant increase in the number of participants. We conclude with emphasizing the value we see with organizing for participation in the transformation of higher education.

Place, publisher, year, edition, pages
IEEE, 2021
Keywords
organization, communities of practice, participation, future education, capacity building
National Category
Learning Didactics
Identifiers
urn:nbn:se:kth:diva-319701 (URN)000838125200047 ()
Conference
World Engineering Education Forum (WEEF) / Global-Engineering-Deans-Council (GEDC) Conference, NOV 15-18, 2021, Madrid, SPAIN
Note

Part of proceedings: ISBN 978-1-6654-2488-2

QC 20230117

Available from: 2022-10-26 Created: 2022-10-26 Last updated: 2023-01-17Bibliographically approved
Fiorati, A., Berglund, P., Svedendahl, M. & Tessaro, D. (2020). Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates. Advanced Synthesis and Catalysis, 362(5), 1156-1166
Open this publication in new window or tab >>Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates
2020 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 362, no 5, p. 1156-1166Article in journal (Refereed) Published
Abstract [en]

Abstract The challenging bioamination of hydrophobic substrates has been attained through the employment of a disperse system consisting of a combination of a low polarity solvent (e. g. isooctane or methyl-tert-butylether), a non-ionic surfactant and a minimal amount of water. In these conditions, amine transaminases (ATA) were shown to efficiently carry out the reductive amination of variously substituted cyclohexanones, providing good conversions often coupled with a superior stereoselectivity if compared with the corresponding chemical reductive amination. An array of synthetically useful 4-substituted aminocyclohexanes was consequentially synthesized through biocatalysis, analyzed and stereochemically characterized.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2020
Keywords
biotransformations, amination, multiphase catalysis, enzyme catalysis, diastereoselectivity, chemoenzymatic synthesis
National Category
Biocatalysis and Enzyme Technology
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-269562 (URN)10.1002/adsc.201901434 (DOI)000509595300001 ()2-s2.0-85078666403 (Scopus ID)
Funder
EU, FP7, Seventh Framework Programme
Note

QC 20200608

Available from: 2020-03-09 Created: 2020-03-09 Last updated: 2022-06-26Bibliographically approved
Marx, L., Ríos‐Lombardía, N., Süss, P., Höhne, M., Morís, F., González‐Sabín, J. & Berglund, P. (2020). Chemoenzymatic Synthesis of Sertraline. European Journal of Organic Chemistry, 2020(4), 510-513
Open this publication in new window or tab >>Chemoenzymatic Synthesis of Sertraline
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2020 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2020, no 4, p. 510-513Article in journal (Refereed) Published
Abstract [en]

A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti-depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The bioreduction of the racemic tetralone exhibited excellent enantioselectivity (>99 % ee) and diastereomeric ratio (99:1) at 29 % conversion (the maximum theoretical yield is 50 %) after 7 hours. The resulting (S,S)-alcohol was efficiently oxidized to an enantiopure (S)-ketone, an immediate precursor of sertraline, by using sodium hypochlorite as oxidant and 2-azaadamantane N-oxyl (AZADO) as organocatalyst. Alternative routes aiming at the direct biocatalytic amination using imine reductases and transaminases were unsuccessful.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2020
Keywords
Asymmetric catalysis, Biocatalysis, Ketoreductases, Medicinal chemistry, Synthetic methods
National Category
Biocatalysis and Enzyme Technology
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-266975 (URN)10.1002/ejoc.201901810 (DOI)000507589300001 ()2-s2.0-85078385263 (Scopus ID)
Funder
EU, Horizon 2020, 634200
Note

QC 20200129

Available from: 2020-01-28 Created: 2020-01-28 Last updated: 2022-06-26Bibliographically approved
Land, H., Ruggieri, F., Szekrenyi, A., Fessner, W.-D. & Berglund, P. (2020). Engineering the Active Site of an (S)-Selective Amine Transaminase for Acceptance of Doubly Bulky Primary Amines. Advanced Synthesis and Catalysis, 362(4), 812-821
Open this publication in new window or tab >>Engineering the Active Site of an (S)-Selective Amine Transaminase for Acceptance of Doubly Bulky Primary Amines
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2020 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 362, no 4, p. 812-821Article in journal (Refereed) Published
Abstract [en]

A protein engineering approach for expanding the substrate scope of the (S)-selective Chromobacterium violaceum amine transaminase is presented. Amino acid residues in the small binding pocket of the active site were targeted in order to increase the pocket size for acceptance of primary amines bearing two bulky groups. A highly sensitive fluorescence assay was then used to evaluate the generated enzyme variants for their activity towards propyl- and benzyl-substituted screening substrates. The best variant, L59A/F88A, was successfully applied in the kinetic resolution of 1,2-diphenylethylamine using different conditions and substrate loadings. The variant L59A/F88A generated enantiomerically pure (R)-1,2-diphenylethylamine with ee >99 % under all tested conditions. The variant also holds great promise for synthesis of hydrophobic compounds as it shows optimum activity when 20 % (v/v) DMSO is applied as cosolvent. The variant L59A/F88A provides a great addition to the available catalyst toolbox for synthesis of chiral amines, as it is the first published (S)-selective amine transaminase showing activity towards benzyl-substituted primary amines.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2020
Keywords
Biocatalysis, Enzymes, Kinetic resolution, Aminotransferase, Protein engineering
National Category
Biochemistry and Molecular Biology
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-264573 (URN)10.1002/adsc.201901252 (DOI)000501916200001 ()2-s2.0-85076409853 (Scopus ID)
Note

QC 20191204

Available from: 2019-11-29 Created: 2019-11-29 Last updated: 2024-03-15Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0002-9577-832X

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