130710-56-4Relevant academic research and scientific papers
Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones
N?cker, Christina,Kaiser, Nadine,Foley, Daniel,Sievers, Sonja,Janning, Petra,Waldmann, Herbert,Laraia, Luca
supporting information, (2021/04/22)
Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.
Synthesis of (+)-Tacamonine via Stereoselective Radical Cyclization
Smith, Myles W.,Ferreira, Jasmin,Hunter, Roger,Venter, Gerhard A.,Su, Hong
supporting information, p. 8740 - 8745 (2019/11/11)
A concise, asymmetric synthesis of the indole alkaloid (+)-tacamonine is reported involving a stereoselective radical cyclization of a 1-phenylsulfanyl tetrahydro-β-carboline bearing a pendant enoate ester side chain as a key step. In this process, a sing
Total synthesis of peloruside a through kinetic lactonization and relay ring-closing metathesis cyclization reactions
Hoye, Thomas R.,Jeon, Junha,Kopel, Lucas C.,Ryba, Troy D.,Tennakoon, Manomi A.,Wang, Yini
supporting information; experimental part, p. 6151 - 6155 (2010/11/18)
The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.
Efficient approach to fluvirucins b2-b5, sch 38518, and sch 39185. first synthesis of their aglycon, via CM and RCM reactions
Llacer, Enric,Urpi, Felix,Vilarrasa, Jaume
body text, p. 3198 - 3201 (2009/12/05)
A route to fluvirucinins B2-5 (the common aglycon of fluvirucins B2-B5, Sch 38518, and Sch 39185) is reported for the first time. A ringclosing metathesis (RCM) generated the C6-C7 double bond, which by catalytic hydrogena
Assignment of Stereochemistry in the Oligomycin/Rutamycin/Cytovaricin Family of Antibiotics. Asymmetric Synthesis of the Rutamycin Spiroketal Synthon
Evans, David A.,Rieger, Dale L.,Jones, Todd K.,Kaldor, Stephen W.
, p. 6260 - 6268 (2007/10/02)
The absolute stereochemistry of the rutamycin antibiotics 2a,b has been established through asymmetric synthesis of the known degradation product 4.One of the key steps in the assemblage process involves acylation of the metalated hydrazone 6 with the N-m
Chemical Synthesis of 3-Ethylcompactin, an Inhibitor of 3-Hydroxy-3-methylglutarylcoenzyme A Reductase
Clive, Derrick L. J.,Murthy, K. S. Keshava,George, Rajan,Poznansky, Mark J.
, p. 2099 - 2108 (2007/10/02)
A method is described for stereocontrolled synthesis of (+)-3-ethylcompactin (1c), a compound that inhibits rat liver HMG CoA reductase with a similar potency to mevinolin.The synthetic approach is a general one and involves linking a pent-4-enal (3) with
