22884-84-0

Upstream product

• 1402731-34-3 ethyl 4-hydroxy-4-methyl-3-oxopentanoate 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 107153-46-8 4-acetoxy-5,5-dimethyl-5H-furan-2-one 
• 7646-78-8 tin(IV) chloride 
• 98-95-3 nitrobenzene 
• 110451-07-5 1'-methoxycarbonyl-1'-methylethyl 3-oxobutanoate 
• 50630-62-1 5,5-dimethyl-2,3,4,5-tetrahydro-2,4-furandione 

Relevant academic research and scientific papers

Total syntheses of the gregatins A-D and aspertetronin A: Structure revisions of these compounds and of aspertetronin B, together with plausible structure revisions of gregatin E, cyclogregatin, graminin A, the penicilliols A and B, and the huaspenones A and B

Comprehensive comparisons of 1H and 13C NMR chemical shift values in the furanone cores a, b, and c provide plausible support for a reassessment of the furanone nuclei of the title compounds from b to c. Total syntheses via enantiomerically pure lactic esters were based on the Seebach-Frater "self-reproduction of stereocenters" methodology. Attachment of the hexadienyl side-chain in a trans,trans-selective manner was achieved by addition of the Seebach-Frater enolate to trans-hex-4-en-1-al rather than to trans-hex-3-en-1-al. The type-c furanone cores of the synthetic materials were reached by single or double acylation of a model γ-hydroxy-β-oxo ester (compound 50) and its hexadiene-containing counterpart 29. Our syntheses confirmed the novel connectivities in six compounds. In addition, they required revision of the configuration of a quaternary carbon atom in five cases. Moreover, they allowed elucidation of the configurations of four previously unassigned stereocenters. Hindsight analyses of why the furanone cores of the title compounds had been misinterpreted as a and/or b instead of c are given. Why the stereocenters in the heterocycles had been incorrectly configured, on the bases (a) of relay studies in the 1960s, and (b) of a 1984 total synthesis of gregatin B, is also discussed.

Methods of inhibiting the advanced glycosylation of proteins using tetramic and tetronic acids and compositions therefor

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.