81477-91-0Relevant articles and documents
Synthesis of Chiral Spin-Labeled Amino Acids
Vuong, Wayne,Mosquera-Guagua, Fabricio,Sanichar, Randy,McDonald, Tyler R.,Ernst, Oliver P.,Wang, Lei,Vederas, John C.
supporting information, p. 10149 - 10153 (2019/12/24)
Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.
Solution versus fluorous versus solid-phase synthesis of 2,5-disubstituted 1,3-azoles. Preliminary antibacterial activity studies
Sanz-Cervera, Juan F.,Blasco, Rauel,Piera, Julio,Cynamon, Michael,Ibanez, Ignacio,Murguia, Marcelo,Fustero, Santos
scheme or table, p. 8988 - 8996 (2010/03/24)
(Chemical Equation Presented) A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine with a fluorous tag in the ester moiety is used as a starting material, the synthesis can be easily completed without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.
Oxazole cyclopeptides for chirality transfer in C3-symmetric octahedral metal complexes
Pinter, Aron,Haberhauer, Gebhard
experimental part, p. 2375 - 2387 (2009/04/05)
A straightforward synthesis of C3-symmetric oxazole-containing macrocyclic peptide scaffolds is presented. This type of macrocycles bears three functional groups on the oxazole rings, which allows fixing of various receptor arms on them in an easy manner. The chiral backbone of the macrocycle proved to be a powerful tool for chirality induction, thus predetermining the configuration of helically coordinated metal centres. The diastereoselective formation of CoII, NiII, CuII and Zn II complexes with tripodal bipyridyl ligand 4 was proved by UV- and CD-absorption spectrophotometric titration experiments. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
