Ducho, Christian

[["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","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","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"]]

[["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"]]