112700-42-2Relevant academic research and scientific papers
Cytotoxic tetramic acid derivative produced by a plant type-III polyketide synthase
Wakimoto, Toshiyuki,Mori, Takahiro,Morita, Hiroyuki,Abe, Ikuro
, p. 4746 - 4749 (2011/06/19)
The tetramic acid (2,4-pyrrolidinedione) scaffold has been recognized as an important structural feature because of its mycotoxic, antibacterial, antiviral, and antioxidant activities. This important class of natural products is reportedly produced by the type-I polyketide synthase/nonribosomal peptide synthetase (PKS/NRPS) hybrid megaenzyme systems. In contrast, the benzalacetone synthase (BAS) from Rheum palmatum is a structurally simple, plant-specific type-III PKS that catalyzes the one-step decarboxylative condensation of malonyl-CoA with 4-coumaroyl-CoA. The type-III PKS exhibits unusually broad substrate specificity and notable catalytic versatility. Here we report that R. palmatum BAS efficiently produces a series of unnatural, novel tetramic acid derivatives by the condensation of malonyl-CoA with aminoacyl-CoA thioesters chemically synthesized from l- and d-amino acids. Remarkably, the novel tetramic acid dimer d-5 formed from d-phenylalanoyl-CoA showed moderate antiproliferative activity against murine leukemia P388 cells.
Design of potential new HIV protease inhibitors: Enantioconvergent synthesis of new pyrrolidin-3-ol, and pyrrolidin-3-one peptide conjugates
Courcambeck,Bihel,De Michelis,Quelever,Kraus
, p. 1421 - 1430 (2007/10/03)
Novel potential HIV protease inhibitors are obtained by an enantioconvergent synthesis of mimicking Phe-Pro dipeptides, achieved through the coupling between Boc(L)Phe or Boc(L)Tyr and both enantiomers of syn-2-benzylpyrrolidin-3-ol and their correspondin
Stereospecific Synthesis of N-Protected Statine and Its Analogues via Chiral Tetramic Acid
Jouin, Patrick,Castro, Bertrand,Nisato, Dino
, p. 1177 - 1182 (2007/10/02)
The condensation of a chiral N-protected amino acid with Meldrum's acid in the presence of isopropenyl chloroformate (IPCF) and of 4-N,N-dimethylaminopyridine (DMAP) has been examined.The cyclisation of the reaction product, by heating in an organic solve
