Ducho, Christian

[["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","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","13742"],["dc.bibliographiccitation.issue","89"],["dc.bibliographiccitation.journal","Chemical Communications"],["dc.bibliographiccitation.lastpage","13745"],["dc.bibliographiccitation.volume","50"],["dc.contributor.author","Schmidtgall, Boris"],["dc.contributor.author","Spork, Anatol P."],["dc.contributor.author","Wachowius, Falk"],["dc.contributor.author","Hobartner, Claudia"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T09:45:43Z"],["dc.date.available","2018-11-07T09:45:43Z"],["dc.date.issued","2014"],["dc.description.abstract","The nucleosyl amino acid (NAA)-modification of oligonucleotides is introduced, which enables the preparation of oligonucleotides with zwitterionic backbone structures. It is demonstrated that partially zwitterionic NAA-modified DNA oligonucleotides are capable of duplex formation with native polyanionic counterstrands and show retained sensitivity towards base-pairing mismatches."],["dc.identifier.doi","10.1039/c4cc06371f"],["dc.identifier.isi","000343988200025"],["dc.identifier.pmid","25251903"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/34687"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Royal Soc Chemistry"],["dc.relation.issn","1364-548X"],["dc.relation.issn","1359-7345"],["dc.title","Synthesis and properties of DNA oligonucleotides with a zwitterionic backbone structure"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","2323"],["dc.bibliographiccitation.issue","10"],["dc.bibliographiccitation.journal","Organic & Biomolecular Chemistry"],["dc.bibliographiccitation.lastpage","2326"],["dc.bibliographiccitation.volume","8"],["dc.contributor.author","Spork, Anatol P."],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T08:48:21Z"],["dc.date.available","2018-11-07T08:48:21Z"],["dc.date.issued","2010"],["dc.description.abstract","Naturally occurring nucleoside antibiotics such as muraymycins represent promising lead structures for the development of novel antibacterial agents. A concise synthesis of 5 '-deoxy muraymycin derivatives has been developed. The key step was the highly stereoselective asymmetric hydrogenation of suitable didehydro amino acid precursors, providing unique nucleosyl amino acid structures."],["dc.identifier.doi","10.1039/c003092a"],["dc.identifier.isi","000277399300006"],["dc.identifier.pmid","20386790"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/21181"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Royal Soc Chemistry"],["dc.relation.issn","1477-0520"],["dc.title","Novel 5 '-deoxy nucleosyl amino acid scaffolds for the synthesis of muraymycin analogues"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","763"],["dc.bibliographiccitation.issue","7"],["dc.bibliographiccitation.journal","Tetrahedron Asymmetry"],["dc.bibliographiccitation.lastpage","766"],["dc.bibliographiccitation.volume","21"],["dc.contributor.author","Spork, Anatol P."],["dc.contributor.author","Koppermann, Stefan"],["dc.contributor.author","Dittrich, Birger"],["dc.contributor.author","Herbst-Irmer, Regine"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T08:43:59Z"],["dc.date.available","2018-11-07T08:43:59Z"],["dc.date.issued","2010"],["dc.description.abstract","The reaction of protected uridine 5'-aldehydes with sulfur ylides has been reinvestigated Further transformation of the resulting epoxide product provided a compound of which a single crystal for X-ray diffraction was obtained. As a consequence from the elucidated structure, the stereochemical configuration of the epoxide furnished by the sulfur ylide reaction was revised. Based on these results, an efficient synthesis of the core structure of the naturally occurring muraymycin and caprazamycin nucleoside antibiotics was developed. (C) 2010 Elsevier Ltd. All rights reserved"],["dc.identifier.doi","10.1016/j.tetasy.2010.03.037"],["dc.identifier.isi","000279493400001"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/20106"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Pergamon-elsevier Science Ltd"],["dc.relation.issn","0957-4166"],["dc.title","Efficient synthesis of the core structure of muraymycin and caprazamycin nucleoside antibiotics based on a stereochemically revised sulfur ylide reaction"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]