Ducho, Christian

[["dc.bibliographiccitation.firstpage","440"],["dc.bibliographiccitation.issue","04"],["dc.bibliographiccitation.journal","Synlett"],["dc.bibliographiccitation.lastpage","446"],["dc.bibliographiccitation.volume","29"],["dc.contributor.author","Wiegmann, Daniel"],["dc.contributor.author","Spork, Anatol"],["dc.contributor.author","Niro, Giuliana"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2020-12-10T18:12:15Z"],["dc.date.available","2020-12-10T18:12:15Z"],["dc.date.issued","2018"],["dc.identifier.doi","10.1055/s-0036-1591517"],["dc.identifier.eissn","1437-2096"],["dc.identifier.issn","0936-5214"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/74304"],["dc.language.iso","en"],["dc.notes.intern","DOI Import GROB-354"],["dc.title","Thieme Chemistry Journals Awardees – Where Are They Now? ­Ribosylation of an Acid-Labile Glycosyl Acceptor as a Potential Key Step for the Synthesis of Nucleoside Antibiotics"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","15292"],["dc.bibliographiccitation.issue","47"],["dc.bibliographiccitation.journal","Chemistry - A European Journal"],["dc.bibliographiccitation.lastpage","15297"],["dc.bibliographiccitation.volume","20"],["dc.contributor.author","Spork, Anatol P."],["dc.contributor.author","Bueschleb, Martin"],["dc.contributor.author","Ries, Oliver"],["dc.contributor.author","Wiegmann, Daniel"],["dc.contributor.author","Boettcher, Stefan"],["dc.contributor.author","Mihalyi, Agnes"],["dc.contributor.author","Bugg, Timothy D. H."],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T09:32:36Z"],["dc.date.available","2018-11-07T09:32:36Z"],["dc.date.issued","2014"],["dc.description.abstract","Naturally occurring muraymycin nucleoside antibiotics represent a promising class of novel antibacterial agents. The structural complexity suggests the investigation of simplified analogues as potential lead structures, which can then be further optimized towards highly potent antimicrobials. Herein we report studies on muraymycin-derived potential lead structures lacking an aminoribose motif found in most naturally occurring muraymycins. We have identified a 5'-defunctionalized motif to be ideal in terms of stability and chemical accessibility and have synthesized a full-length muraymycin analogue based on this structure using a novel fully stereocontrolled route. The obtained 5'-deoxy analogue of the natural product muraymycin C4 showed good inhibitory properties towards the bacterial target protein MraY, sufficient pharmacokinetic stability and no cytotoxicity against human cells, thus making it a promising lead for antibacterial drug development."],["dc.identifier.doi","10.1002/chem.201404775"],["dc.identifier.isi","000345234800002"],["dc.identifier.pmid","25318977"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/31787"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Wiley-v C H Verlag Gmbh"],["dc.relation.issn","1521-3765"],["dc.relation.issn","0947-6539"],["dc.title","Lead Structures for New Antibacterials: Stereocontrolled Synthesis of a Bioactive Muraymycin Analogue"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","2503"],["dc.bibliographiccitation.issue","15"],["dc.bibliographiccitation.journal","Synlett"],["dc.bibliographiccitation.lastpage","2507"],["dc.contributor.author","Spork, Anatol P."],["dc.contributor.author","Koppermann, Stefan"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T11:24:15Z"],["dc.date.available","2018-11-07T11:24:15Z"],["dc.date.issued","2009"],["dc.description.abstract","Nucleoside antibiotics represent a promising class of natural products for the development of novel antibacterial agents, with particular respect to structurally simplified analogues maintaining biological activity. There are established truncated 5'-epi-derivatives of muraymycin nucleoside antibiotics with reported antibacterial properties, but the lengthy preparation Of Such compounds is a major hurdle in more detailed structure-activity relationship (SAR) studies. A concise, improved synthesis of truncated 5'-epi-muraymycins based on a previously reported approach using sulfur ylide chemistry is reported here. The highly convergent nature of this strategy will allow the efficient synthesis of novel muraymycin analogues for thorough SAR investigations."],["dc.identifier.doi","10.1055/s-0029-1217742"],["dc.identifier.isi","000270593200026"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/56360"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Georg Thieme Verlag Kg"],["dc.relation.issn","0936-5214"],["dc.title","Improved Convergent Synthesis of 5 '-epi-Analogues of Muraymycin Nucleoside Antibiotics"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","879"],["dc.bibliographiccitation.issue","5"],["dc.bibliographiccitation.journal","MedChemComm"],["dc.bibliographiccitation.lastpage","886"],["dc.bibliographiccitation.volume","6"],["dc.contributor.author","Ries, Oliver"],["dc.contributor.author","Carnarius, Christian"],["dc.contributor.author","Steinem, Claudia"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2015-07-17T07:56:31Z"],["dc.date.accessioned","2021-10-27T13:12:17Z"],["dc.date.available","2015-07-17T07:56:31Z"],["dc.date.available","2021-10-27T13:12:17Z"],["dc.date.issued","2015"],["dc.description.abstract","Functional insights into bioactive natural products with medicinal potential are often hindered by their structural complexity. We herein report a simplified model system to investigate the functional significance of a structural motif of biologically potent muraymycin antibiotics of the A-series. These compounds have a highly unusual ω-guanidinylated fatty acid moiety, which has been proposed to mediate membrane penetration, thus enabling the interaction of A-series muraymycins with their intracellular target MraY. Our assay was based on a synthetic conjugate of this fatty acid structure with a negatively charged fluorophore lacking membrane permeability. Using this conjugate, immobilised giant unilamellar lipid vesicles and confocal laser scanning fluorescence microscopy, we demonstrated that the attachment of the ω-N-hydroxyguanidinyl fatty acid unit led to an enhanced uptake of the fluorophore into the vesicles. This represents the first experimental evidence of this unusual structural motif's functional relevance for the parent natural product, which may support the future design of novel muraymycin analogues."],["dc.identifier.doi","10.1039/c4md00526k"],["dc.identifier.gro","3141982"],["dc.identifier.isi","000354437800016"],["dc.identifier.purl","https://resolver.sub.uni-goettingen.de/purl?gs-1/11974"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/91677"],["dc.language.iso","en"],["dc.notes.intern","Migrated from goescholar"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.eissn","2040-2511"],["dc.relation.issn","2040-2511"],["dc.relation.issn","2040-2503"],["dc.relation.orgunit","Fakultät für Chemie"],["dc.rights","Goescholar"],["dc.rights.access","openAccess"],["dc.rights.uri","https://goescholar.uni-goettingen.de/licenses"],["dc.subject","fatty acid; moiety; muraymycin antibiotics; Membrane-interacting"],["dc.title","Membrane-interacting properties of the functionalised fatty acid moiety of muraymycin antibiotics"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dc.type.version","published_version"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","6697"],["dc.bibliographiccitation.issue","30"],["dc.bibliographiccitation.journal","Angewandte Chemie International Edition"],["dc.bibliographiccitation.lastpage","6700"],["dc.bibliographiccitation.volume","50"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T09:00:22Z"],["dc.date.available","2018-11-07T09:00:22Z"],["dc.date.issued","2011"],["dc.description.sponsorship","Junior Scientist Program (JSP)"],["dc.identifier.doi","10.1002/anie.201103875"],["dc.identifier.isi","000292774200001"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/24143"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Wiley-blackwell"],["dc.relation.issn","1433-7851"],["dc.title","A Kaleidoscope of Contemporary Organic Chemistry: The 46th Burgenstock Conference"],["dc.type","review"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","10083"],["dc.bibliographiccitation.issue","24"],["dc.bibliographiccitation.journal","The Journal of Organic Chemistry"],["dc.bibliographiccitation.lastpage","10098"],["dc.bibliographiccitation.volume","76"],["dc.contributor.author","Spork, Anatol P."],["dc.contributor.author","Wiegmann, Daniel"],["dc.contributor.author","Granitzka, Markus"],["dc.contributor.author","Stalke, Dietmar"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T08:48:51Z"],["dc.date.available","2018-11-07T08:48:51Z"],["dc.date.issued","2011"],["dc.description.abstract","Novel hybrid structures of 5'-deoxyuridine and glycine were conceived and synthesized. Such nucleosyl amino acids (NAAs) represent simplified analogues of the core structure of muraymycin nucleoside antibiotics, making them useful synthetic building blocks for structure-activity relationship (SAR) studies. The key step of the developed synthetic route was the efficient and highly diastereoselective asymmetric hydrogenation of didehydro amino acid precursors toward protected NAA.s. It was anticipated that the synthesis of unprotected muraymycin derivatives via this route would require a suitable intermediate protecting group at the N-3 of the uracil base. After initial attempts using PMB- and BOM-N-3 protection, both of which resulted in problematic deprotection steps, an N-3 protecting group-free route was envisaged. In spite of the pronounced acidity of the uracil-3-NH, this route worked equally efficient and with identical stereoselectivities as the initial strategies involving N-3 protection. The obtained NAA building blocks were employed for the synthesis of truncated 5'-deoxymuraymycin analogues."],["dc.identifier.doi","10.1021/jo201935w"],["dc.identifier.isi","000297715900021"],["dc.identifier.pmid","22059552"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/21318"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Amer Chemical Soc"],["dc.relation.issn","0022-3263"],["dc.title","Stereoselective Synthesis of Uridine-Derived Nucleosyl Amino Acids"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","2313"],["dc.bibliographiccitation.issue","6"],["dc.bibliographiccitation.journal","Amino Acids"],["dc.bibliographiccitation.lastpage","2328"],["dc.bibliographiccitation.volume","43"],["dc.contributor.author","Bueschleb, Martin"],["dc.contributor.author","Granitzka, Markus"],["dc.contributor.author","Stalke, Dietmar"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T09:03:02Z"],["dc.date.available","2018-11-07T09:03:02Z"],["dc.date.issued","2012"],["dc.description.abstract","The non-proteinogenic amino acids capreomycidine and epicapreomycidine are constituents of antibiotically active natural products, but the synthesis of these unusual cyclic guanidine derivatives is challenging. The biosynthesis of capreomycidine has therefore been employed as a guideline to develop a concise biomimetic synthesis of both epimeric amino acids. The resulting domino-guanidinylation-aza-Michael-addition reaction provides the most convenient access to these amino acids in racemic form. Attempts to dissect the domino reaction into two separate transformations for a stereocontrolled version of this synthetic approach have also been made. The synthesized didehydro-arginine derivatives with urethane-protected guanidine moieties did not undergo the aza-Michael-addition anymore. These results may have wider implications for the 1,4-addition of guanidines to alpha,beta-unsaturated carbonyl compounds, particularly to didehydro amino acids."],["dc.identifier.doi","10.1007/s00726-012-1309-8"],["dc.identifier.isi","000310885500009"],["dc.identifier.pmid","22619064"],["dc.identifier.purl","https://resolver.sub.uni-goettingen.de/purl?gs-1/8826"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/24810"],["dc.notes.intern","Merged from goescholar"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Springer"],["dc.publisher.place","Wien"],["dc.relation.issn","1438-2199"],["dc.relation.issn","0939-4451"],["dc.rights","Goescholar"],["dc.rights.uri","https://goescholar.uni-goettingen.de/licenses"],["dc.title","A biomimetic domino reaction for the concise synthesis of capreomycidine and epicapreomycidine"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dc.type.version","published_version"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","208"],["dc.bibliographiccitation.issue","1"],["dc.bibliographiccitation.journal","Tetrahedron"],["dc.bibliographiccitation.lastpage","214"],["dc.bibliographiccitation.volume","66"],["dc.contributor.author","Lemke, Anke"],["dc.contributor.author","Bueschleb, Martin"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T08:46:49Z"],["dc.date.available","2018-11-07T08:46:49Z"],["dc.date.issued","2010"],["dc.description.abstract","The hydroxylated amino acid 3-hydroxy-L-arginine is an intermediate in the biosynthesis of the non-proteinogenic amino acid capreomycidine and possibly also of its epimer epicapreomycidine. The novel concise synthesis of 3-hydroxy-L-arginine presented here allows the efficient preparation of both 3-epimers of this beta-hydroxy amino acid. It also offers the potential to obtain suitably isotope-labelled derivatives for the elucidation of epicapreomycidine assembly in the biosynthesis of complex natural products. (C) 2009 Elsevier Ltd. All rights reserved."],["dc.description.sponsorship","Fonds der Chemischen Industrie (FCI)"],["dc.identifier.doi","10.1016/j.tet.2009.10.102"],["dc.identifier.isi","000273066200022"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/20789"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Pergamon-elsevier Science Ltd"],["dc.relation.issn","0040-4020"],["dc.title","Concise synthesis of both diastereomers of 3-hydroxy-L-arginine"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","50"],["dc.bibliographiccitation.journal","Beilstein Journal of Organic Chemistry"],["dc.bibliographiccitation.lastpage","59"],["dc.bibliographiccitation.volume","11"],["dc.contributor.author","Schmidtgall, Boris"],["dc.contributor.author","Hoebartner, Claudia"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T10:02:12Z"],["dc.date.available","2018-11-07T10:02:12Z"],["dc.date.issued","2015"],["dc.description.abstract","Modifications of the nucleic acid backbone are essential for the development of oligonucleotide-derived bioactive agents. The NAA-modification represents a novel artificial internucleotide linkage which enables the site-specific introduction of positive charges into the otherwise polyanionic backbone of DNA oligonucleotides. Following initial studies with the introduction of the NAA-linkage at T-T sites, it is now envisioned to prepare NAA-modified oligonucleotides bearing the modification at X-T motifs (X = A, C, G). We have therefore developed the efficient and stereoselective synthesis of NAA-linked 'dimeric' A-T phosphoramidite building blocks for automated DNA synthesis. Both the (S)- and the (R)-configured NAA-motifs were constructed with high diastereoselectivities to furnish two different phosphoramidite reagents, which were employed for the solid phase-supported automated synthesis of two NAA-modified DNA oligonucleotides. This represents a significant step to further establish the NAA-linkage as a useful addition to the existing 'toolbox' of backbone modifications for the design of bioactive oligonucleotide analogues."],["dc.identifier.doi","10.3762/bjoc.11.8"],["dc.identifier.isi","000348469500001"],["dc.identifier.pmid","25670992"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/38182"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Beilstein-institut"],["dc.relation.issn","1860-5397"],["dc.title","NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A-T phosphoramidite building blocks"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","2868"],["dc.bibliographiccitation.issue","11"],["dc.bibliographiccitation.journal","Molecules"],["dc.bibliographiccitation.volume","23"],["dc.contributor.author","Spork, Anatol"],["dc.contributor.author","Koppermann, Stefan"],["dc.contributor.author","Schier (née Wohnig), Stephanie"],["dc.contributor.author","Linder, Ruth"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2020-12-10T18:47:16Z"],["dc.date.available","2020-12-10T18:47:16Z"],["dc.date.issued","2018"],["dc.description.sponsorship","Deutsche Forschungsgemeinschaft"],["dc.identifier.doi","10.3390/molecules23112868"],["dc.identifier.eissn","1420-3049"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/78702"],["dc.language.iso","en"],["dc.notes.intern","DOI Import GROB-354"],["dc.publisher","MDPI"],["dc.relation.eissn","1420-3049"],["dc.rights","https://creativecommons.org/licenses/by/4.0/"],["dc.title","Analogues of Muraymycin Nucleoside Antibiotics with Epimeric Uridine-Derived Core Structures"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dspace.entity.type","Publication"]]