Ducho, Christian

[["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","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"]]