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","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","924"],["dc.bibliographiccitation.issue","8"],["dc.bibliographiccitation.journal","Macromolecular Chemistry and Physics"],["dc.bibliographiccitation.lastpage","933"],["dc.bibliographiccitation.volume","214"],["dc.contributor.author","Meiser, Wibke"],["dc.contributor.author","Buback, Michael"],["dc.contributor.author","Ries, Oliver"],["dc.contributor.author","Ducho, Christian"],["dc.contributor.author","Sidoruk, Alana"],["dc.date.accessioned","2018-11-07T09:25:53Z"],["dc.date.available","2018-11-07T09:25:53Z"],["dc.date.issued","2013"],["dc.description.abstract","The reversible additionfragmentation chain transfer (RAFT) equilibrium constant of the phenylethyl1-phenylethyl dithiobenzoate model system is deduced via EPR spectroscopy to be 31 +/- 4 L mol1 at 110 degrees C. The difference in activation energies of addition and fragmentation, Ea(kad) Ea(k) approximate to 45.6 kJ mol1, is close to that of the polystyrylpolystyryl dithiobenzoate system. Significant amounts of products from cross-termination and from missing step reaction of the cross-termination product with the phenylethyl radical demonstrate that intermediate radical termination, rather than slow fragmentation of the RAFT intermediate radical, is responsible for the rate retardation in the dithiobenzoate-mediated styrene polymerization."],["dc.identifier.doi","10.1002/macp.201200668"],["dc.identifier.isi","000318028700007"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/30166"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Wiley-v C H Verlag Gmbh"],["dc.relation.issn","1022-1352"],["dc.title","EPR Study into Cross-Termination and Fragmentation with the PhenylethylPhenylethyl Dithiobenzoate RAFT Model System"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","2357"],["dc.bibliographiccitation.issue","15"],["dc.bibliographiccitation.journal","Synthesis"],["dc.bibliographiccitation.lastpage","2368"],["dc.contributor.author","Ries, Oliver"],["dc.contributor.author","Ochmann, Anne"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T08:53:51Z"],["dc.date.available","2018-11-07T08:53:51Z"],["dc.date.issued","2011"],["dc.description.abstract","Representing a prime example of the interesting structures found in natural products, the N-alkyl-N-hydroxyguanidine moiety has so far only found limited attention in synthetic organic chemistry. Our studies on Streptomyces-produced muraymycin nucleoside antibiotics have led to a systematic investigation of the synthetic access to the N-hydroxyguanidine-functionalized lipid structure of biologically potent A-series muraymycins. A protecting-group-free approach has been proven to be superior to a strategy employing highly reactive urethane-protected guanidinylation reagents, particularly due to the unexpected instability of fully protected N-alkyl-N-hydroxyguanidines. The protecting-group-free method has been used for the synthesis of other N-alkyl-N-hydroxyguanidine derivatives, namely the antibiotic N(5)-hydroxy-L-arginine. These synthetic results will enable the elucidation of the properties and biological significance of the N-alkyl-N-hydroxyguanidine functionality."],["dc.identifier.doi","10.1055/s-0030-1260100"],["dc.identifier.isi","000292961400005"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/22527"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Georg Thieme Verlag Kg"],["dc.relation.issn","0039-7881"],["dc.title","Synthesis of N-Alkyl-N-hydroxyguanidines: A Comparative Study Using Different Protecting Group Strategies"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","1135"],["dc.bibliographiccitation.journal","Beilstein Journal of Organic Chemistry"],["dc.bibliographiccitation.lastpage","1142"],["dc.bibliographiccitation.volume","10"],["dc.contributor.author","Ries, Oliver"],["dc.contributor.author","Bueschleb, Martin"],["dc.contributor.author","Granitzka, Markus"],["dc.contributor.author","Stalke, Dietmar"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T09:40:12Z"],["dc.date.available","2018-11-07T09:40:12Z"],["dc.date.issued","2014"],["dc.description.abstract","(2S,3S)-3-Hydroxyleucine can be found in an increasing number of bioactive natural products. Within the context of our work regarding the total synthesis of muraymycin nucleoside antibiotics, we have developed a synthetic approach towards (2S,3S)-3-hydroxyleucine building blocks. Application of different protecting group patterns led to building blocks suitable for C- or N-terminal derivatization as well as for solid-phase peptide synthesis. With respect to according motifs occurring in natural products, we have converted these building blocks into 3-O-acylated structures. Utilizing an esterification and cross-metathesis protocol, (2S,3S)-3-hydroxyleucine derivatives were synthesized, thus opening up an excellent approach for the synthesis of bioactive natural products and derivatives thereof for structure activity relationship (SAR) studies."],["dc.identifier.doi","10.3762/bjoc.10.113"],["dc.identifier.isi","000335990800001"],["dc.identifier.pmid","24991264"],["dc.identifier.purl","https://resolver.sub.uni-goettingen.de/purl?gs-1/11912"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/33454"],["dc.notes.intern","Merged from goescholar"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Beilstein-institut"],["dc.relation.issn","1860-5397"],["dc.rights","CC BY 2.0"],["dc.rights.uri","https://creativecommons.org/licenses/by/2.0"],["dc.title","Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine"],["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","2876"],["dc.bibliographiccitation.issue","21"],["dc.bibliographiccitation.journal","Synthetic Communications"],["dc.bibliographiccitation.lastpage","2882"],["dc.bibliographiccitation.volume","43"],["dc.contributor.author","Ries, Oliver"],["dc.contributor.author","Granitzka, Markus"],["dc.contributor.author","Stalke, Dietmar"],["dc.contributor.author","Ducho, Christian"],["dc.date.accessioned","2018-11-07T09:17:42Z"],["dc.date.available","2018-11-07T09:17:42Z"],["dc.date.issued","2013"],["dc.description.abstract","Stem cell research is one of the most promising fields of modern biomedical research and regenerative medicine. Limited availability and ethical concerns suggest the renouncement of embryonic stem cells (ESCs), thus raising the need for more efficient procedures for the generation of stem cells, ideally through reprogramming of mammalian cells. The small molecule N-benzyl-2-(pyrimidin-4-ylamino)-thiazole-4-carboxamide (thiazovivin) is known to improve the generation of human induced pluripotent stem cells (iPSCs) from human fibroblasts. We herein describe a highly efficient procedure for the synthesis of thiazovivin over just five steps, which should be suitable for a large-scale application, and the first x-ray crystal structure of the target compound. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]"],["dc.identifier.doi","10.1080/00397911.2012.745567"],["dc.identifier.isi","000322307500006"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/28229"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Taylor & Francis Inc"],["dc.relation.issn","1532-2432"],["dc.relation.issn","0039-7911"],["dc.title","Concise Synthesis and X-Ray Crystal Structure of N-Benzyl-2-(pyrimidin-4-ylamino)-thiazole-4-carboxamide (Thiazovivin), a Small-Molecule Tool for Stem Cell Research"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]