19717-14-7Relevant articles and documents
Cystobactamids 920-1 and 920-2: Assignment of the Constitution and Relative Configuration by Total Synthesis
Planke, Therese,Moreno, María,Hüttel, Stephan,Fohrer, J?rg,Gille, Franziska,Norris, Matthew D.,Siebke, Maik,Wang, Liangliang,Müller, Rolf,Kirschning, Andreas
supporting information, p. 1359 - 1363 (2019/03/08)
Total synthesis of cystobactamid 920-1 and its epimer has allowed an unambiguous assignment of the relative and absolute configuration of the natural product. A careful structural analysis of each isomer using both NMR and computational techniques also pr
Scalable Syntheses of Methoxyaspartate and Preparation of the Antibiotic Cystobactamid 861-2 and Highly Potent Derivatives
Moeller, Malte,Norris, Matthew D.,Planke, Therese,Cirnski, Katarina,Herrmann, Jennifer,Müller, Rolf,Kirschning, Andreas
, p. 8369 - 8372 (2019/10/16)
An improved scalable synthesis of orthogonally functionalized methoxyaspartate, the chiral hinge region element in cystobactamids, is reported. This improvement sets the stage for the total synthesis of four new cystobactamids along with cystobactamid 861
Total Synthesis and Biological Assessment of Novel Albicidins Discovered by Mass Spectrometric Networking
von Eckardstein, Leonard,Petras, Daniel,Dang, Tam,Cociancich, Stéphane,Sabri, Souhir,Gr?tz, Stefan,Kerwat, Dennis,Seidel, Maria,Pesic, Alexander,Dorrestein, Pieter C.,Royer, Monique,Weston, John B.,Süssmuth, Roderich D.
, p. 15316 - 15321 (2017/10/20)
Natural products represent an important source of potential novel antimicrobial drug leads. Low production by microorganisms in cell culture often delays the structural elucidation or even prevents a timely discovery. Starting from the anti-Gram-negative antibacterial compound albicidin produced by Xanthomonas albilineans, we describe a bioactivity-guided approach combined with non-targeted tandem mass spectrometry and spectral (molecular) networking for the discovery of novel antimicrobial compounds. We report eight new natural albicidin derivatives, four of which bear a β-methoxy cyanoalanine or β-methoxy asparagine as the central α-amino acid. We present the total synthesis of these albicidins, which facilitated the unambiguous determination of the (2 S,3 R)-stereoconfiguration which is complemented by the assessment of the stereochemistry on antibacterial activity.