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Publications

Püllmann, P.; Weissenborn, M. J.; Pilzliche Peroxygenasen: der Schlüssel zu C-H-Hydroxylierungen und mehr? BIOspektrum 25 572-574 (2019) DOI: 10.1007/s12268-019-1090-2
  • Abstract
  • Internet
  • BibText
  • RIS

Fungal peroxygenases represent an exciting new enzyme class for stereo-selective hydroxylation reactions. They are capable of the oxyfunctionalisation of a large, diverse scope of substrates including alkanes and steroids as well as the heteroatoms sulfur and nitrogen. The outstanding activities and stabilities as well as their reliance on hydrogen peroxide as co-substrate renders it a highly interesting biocatalyst.

Publications

Kammel, M.; Knorrscheidt, A.; Püllmann, P.; Weissenborn, M. J.; Tackling the numbers problem: Entwicklung nicht-nativer Enzymreaktionen BIOspektrum 23 830-832 (2017) DOI: 10.1007/s12268-017-0876-3
  • Abstract
  • BibText
  • RIS

The screening effort of large protein variant libraries renders the probability of coincidental discovering a new enzyme with non-natural activity to almost zero - the so-called numbers problem. Insights into the origin of life, evolution and enzymatic promiscuity, combined with the inspiration of methods from organic chemistry, offer solutions for this problem. With the newly discovered enzymes synthetic micro production units shall be established in a Leibniz Research Cluster where engineering and biotechnology are combined.

Publications

Welsch, S. J.; Umkehrer, M.; Kalinski, C.; Ross, G.; Burdack, C.; Kolb, J.; Wild, M.; Ehrlich, A.; Wessjohann, L. A.; Synthesis of substituted imidazolines by an Ugi/Staudinger/aza-Wittig sequence Tetrahedron Lett. 56 1025-1029 (2015) DOI: 10.1016/j.tetlet.2015.01.043
  • Abstract
  • BibText
  • RIS

A series of 2-(acetamide-2-yl)-imidazolines (II) with 5 points of diversity were prepared by an Ugi-4CR–Staudinger–aza-Wittig-sequence starting from simple azidoalkylamines. The intramolecular aza-Wittig cyclization between the iminophosphane and the tertiary amide of the Ugi product (I) was effected by short microwave irradiation. Competitive cyclization to the secondary amide was not relevant, however, in some cases subsequent formation of the bicyclic ortho-amidines (III) was observed.

Publications

Lira, L. M.; Vasilev, D.; Pilli, R. A.; Wessjohann, L. A.; One-pot synthesis of organophosphate monoesters from alcohols Tetrahedron Lett. 54 1690-1692 (2013) DOI: 10.1016/j.tetlet.2013.01.059
  • Abstract
  • BibText
  • RIS

A one-pot procedure for the phosphorylation of alcohols provides the corresponding phosphate monoesters in improved yields. The protocol features the use of tetrabutylammonium hydrogen phosphate and trichloroacetonitrile, followed by purification of the crude product by flash chromatography on silica gel. The final step, cation exchange chromatography, affords the organophosphates as ammonium salts that are usually required for biochemical applications. The mechanism appears to be phosphate rather than alcohol activation by trichloroacetonitrile.

Publications

Berger, R.; Bornscheuer, U.; Liese, A.; Schwaneberg, U.; Syldatk, C.; Wessjohann, L.; Biotechnologie von Morgen: DECHEMA/VAAM-Fachgruppe „Biotransformationen“ BIOspektrum 19 208-210 (2013) DOI: 10.1007/s12268-013-0291-3
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0

Publications

Neves Filho, R. A. W.; Stark, S.; Morejon, M. C.; Westermann, B.; Wessjohann, L. A.; 4-Isocyanopermethylbutane-1,1,3-triol (IPB): a convertible isonitrile for multicomponent reactions Tetrahedron Lett. 53 5360-5363 (2012) DOI: 10.1016/j.tetlet.2012.07.064
  • Abstract
  • BibText
  • RIS

The synthesis and applications of 4-isocyanopermethylbutane-1,1,3-triol (IPB) as a new convertible isonitrile (isocyanide) for isocyanide-based multicomponent reactions (IMCRs) like Ugi, Ugi-Smiles, and Passerini reactions are described. The primary products obtained from these IMCRs can be converted into highly activated N-acylpyrroles, which upon treatment with nucleophiles can be transformed into carboxylic acids, esters, amides, alcohols, and olefins. In this sense the reagent can be seen as a neutral carbanion equivalent to formate (HO2C−), and carboxylates or carboxamides etc. (RNu-CO−).

Publications

Wessjohann, L.; Vogt, T.; Kufka, J.; Klein, R.; Prenyl- und Methyltransferasen in Natur und Synthese BIOspektrum 18 22-25 (2012) DOI: 10.1007/s12268-012-0137-4
  • Abstract
  • BibText
  • RIS

Late stage enzymatic prenylation and methylation are means to diversify (natural) compounds and to specify their functions. In eukaryotes and microbes, these steps are performed by large enzyme families, the prenyl and methyl transferases, which modify various types of small molecules, like isoprenoids, phenolics or alkaloids, but also DNA and proteins. We investigate the theoretical basis of these processes and possible commercial applications in synthetic chemistry.

Publications

Welsch, S. J.; Kalinski, C.; Umkehrer, M.; Ross, G.; Kolb, J.; Burdack, C.; Wessjohann, L. A.; Palladium and copper catalyzed cyclizations of hydrazine derived Ugi products: facile synthesis of substituted indazolones and hydroxytriazafluorendiones Tetrahedron Lett. 53 2298-2301 (2012) DOI: 10.1016/j.tetlet.2012.02.095
  • Abstract
  • BibText
  • RIS

Indazolones are medicinally relevant targets. Herein we disclose an improved synthesis to N′-(acetamido-2-yl)-substituted indazolones with four points of diversity introduced by Ugi-[M]-amination and -amidation. The ring closure can be achieved by either conventional palladium catalysis or with a ligandless copper protocol. When α-unbranched isocyanides were employed the sole cyclization products of the copper catalyzed reactions are the hitherto undescribed 2-hydroxy-3H-3,4a,9a-triaza-fluorene-4,9-diones.

Publications

Welsch, S. J.; Umkehrer, M.; Ross, G.; Kolb, J.; Burdack, C.; Wessjohann, L. A.; PdII/IV catalyzed oxidative cyclization of 1,6-enynes derived by Ugi-4-component reaction Tetrahedron Lett. 52 6295-6297 (2011) DOI: 10.1016/j.tetlet.2011.09.094
  • Abstract
  • BibText
  • RIS

A variety of 1,6-enynes were synthesized by an Ugi-reaction and further elaborated by a PdII/IV catalyzed oxidative cyclization to produce N-substituted 3-aza-bicyclo[3.1.0]hexan-2-ones. Different substitution patterns were tested to examine the scope and limitations of the amide tethered substrates.

Publications

Dissmeyer, N.; CDK-Phosphorylierung in Zellzyklus und Stress: artspezifische Unterschiede BIOspektrum 751-753 (2010)
  • Abstract
  • BibText
  • RIS

In Arabidopsis, deactivation of cyclin-dependent kinases via phosphorylation has no function in cell proliferation, growth, and stress response. In other eukaryotes, however, this is mandatorily required for maintaining genomic integrity.

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