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      Ammonia-Promoted One-Pot Tetrazolopiperidinone Synthesis by Ugi Reaction

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          Abstract

          Ammonia in the tetrazole Ugi variation together with α-amino acid methyl ester-derived isocyanides provides tetrazolopiperidinones in good to high yields in one pot. The scope and limitations of this reaction were investigated by performing >70 reactions. The scaffold is useful to fill high-throughput screening decks and in structure-based drug design.

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          2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products.

          Alan Borthwick (2012)
          Article 0 comments Cited 190 times – based on 0 reviews     Review now
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            Rationalizing Tight Ligand Binding through Cooperative Interaction Networks

            Bernd Kuhn, Julian Fuchs, Michael Reutlinger … (2011)
            Small modifications of the molecular structure of a ligand sometimes cause strong gains in binding affinity to a protein target, rendering a weakly active chemical series suddenly attractive for further optimization. Our goal in this study is to better rationalize and predict the occurrence of such interaction hot-spots in receptor binding sites. To this end, we introduce two new concepts into the computational description of molecular recognition. First, we take a broader view of noncovalent interactions and describe protein–ligand binding with a comprehensive set of favorable and unfavorable contact types, including for example halogen bonding and orthogonal multipolar interactions. Second, we go beyond the commonly used pairwise additive treatment of atomic interactions and use a small world network approach to describe how interactions are modulated by their environment. This approach allows us to capture local cooperativity effects and considerably improves the performance of a newly derived empirical scoring function, ScorpionScore. More importantly, however, we demonstrate how an intuitive visualization of key intermolecular interactions, interaction networks, and binding hot-spots supports the identification and rationalization of tight ligand binding.
            Article 0 comments Cited 24 times – based on 0 reviews     Review now
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              Structure-function analysis of an enzymatic prenyl transfer reaction identifies a reaction chamber with modifiable specificity.

              Sylwia Tarcz, Shu Li, Marco Jost … (2010)
              Fungal indole prenyltransferases participate in a multitude of biosynthetic pathways. Their ability to prenylate diverse substrates has attracted interest for potential use in chemoenzymatic synthesis. The fungal indole prenyltransferase FtmPT1 catalyzes the prenylation of brevianamide F in the biosynthesis of fumitremorgin-type alkaloids, which show diverse pharmacological activities and are promising candidates for the development of antitumor agents. Here, we report crystal structures of unliganded Aspergillus fumigatus FtmPT1 as well as of a ternary complex of FtmPT1 bound to brevianamide F and an analogue of its isoprenoid substrate dimethylallyl diphosphate. FtmPT1 assumes a rare α/β-barrel fold, consisting of 10 circularly arranged β-strands surrounded by α-helices. Catalysis is performed in a hydrophobic reaction chamber at the center of the barrel. In combination with mutagenesis experiments, our analysis of the liganded and unliganded structures provides insight into the mechanism of catalysis and the determinants of regiospecificity. Sequence conservation of key features indicates that all fungal indole prenyltransferases possess similar active site architectures. However, while the dimethylallyl diphosphate binding site is strictly conserved in these enzymes, subtle changes in the reaction chamber likely allow for the accommodation of diverse aromatic substrates for prenylation. In support of this concept, we were able to redirect the regioselectivity of FtmPT1 by a single mutation of glycine 115 to threonine. This finding provides support for a potential use of fungal indole prenyltransferases as modifiable bioreactors that can be engineered to catalyze highly specific prenyl transfer reactions.
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Comb Sci
                Journal ID (iso-abbrev): ACS Comb Sci
                Journal ID (publisher-id): co
                Journal ID (coden): acsccc
                Title: ACS Combinatorial Science
                Publisher: American Chemical Society
                ISSN (Print): 2156-8952
                ISSN (Electronic): 2156-8944
                Publication date (Electronic): 27 February 2017
                Publication date (Print): 08 May 2017
                Volume: 19
                Issue: 5
                Pages: 343-350
                Affiliations
                [† ]Drug Design Group, Department of Pharmacy, University of Groningen , Antonius Deusinglaan 1, 9713 AV Groningen, The Netherlands
                [‡ ]Biocrystallography Group, Department of Crystal Chemistry and Crystal Physics, Faculty of Chemistry, Jagiellonian University , Ingardena 3, 30-060 Kraków, Poland
                Author notes
                Article
                DOI: 10.1021/acscombsci.7b00033
                PMC ID: 5424440
                PubMed ID: 28240545
                SO-VID: 2c4b4a13-b219-4916-8462-e429c3d44781
                Copyright © Copyright © 2017 American Chemical Society
                License:

                This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.

                History
                Date received : 15 February 2017
                Categories
                Subject: Research Article
                Custom metadata
                document-id-old-9 co7b00033
                document-id-new-14 co-2017-00033r
                ccc-price

                ScienceOpen disciplines: Biochemistry
                Keywords: tetrazolopiperidinone,isocyanide,multicomponent reaction,ugi reaction,ammonia ugi reaction,european lead factory
                Data availability:
                ScienceOpen disciplines: Biochemistry
                Keywords: tetrazolopiperidinone, isocyanide, multicomponent reaction, ugi reaction, ammonia ugi reaction, european lead factory

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