5457-19-2Relevant articles and documents
Peniphenone and Penilactone Formation in Penicillium crustosum via 1,4-Michael Additions of ortho-Quinone Methide from Hydroxyclavatol to γ-Butyrolactones from Crustosic Acid
Fan, Jie,Liao, Ge,Kindinger, Florian,Ludwig-Radtke, Lena,Yin, Wen-Bing,Li, Shu-Ming
supporting information, p. 4225 - 4229 (2019/03/19)
Penilactones A and B consist of a γ-butyrolactone and two clavatol moieties. We identified two separate gene clusters for the biosynthesis of these key building blocks in Penicillium crustosum. Gene deletion, feeding experiments, and biochemical investiga
A Short Synthesis of the Mould Metabolite (R)-(+)-Carolinic Acid from (S)-Lactic Acid
Linder, David,Schobert, Rainer
, p. 4564 - 4568 (2016/12/14)
(R)-(+)-Carolinic acid was prepared in seven steps and 59% yield from inexpensive benzyl l-lactate, the configuration of which was inverted by a Mitsunobu reaction with trifluoroacetate. The resulting benzyl d-lactate was cyclised by a domino addition-Wittig alkenation reaction with Ph3PCCO. The product tetronic acid was acylated with a second equivalent of this ylide to give a 3-acylylidenetetronic acid, which was olefinated directly with tert-butyl glyoxylate. The product alkene was hydrogenated and deprotected to afford pure crystalline (R)-(+)-carolinic acid, which proved inactive against Staphylococcus aureus and Escherichia coli mutant D21f2.
Methods of inhibiting the advanced glycosylation of proteins using tetramic and tetronic acids and compositions therefor
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, (2008/06/13)
The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises substituted or unsubstituted tetramic and tetronic acids capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with a carbonyl moiety of an early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.