Potential transition-state inhibitors of glyoxalase. I
β Scribed by Richard B. Brandt; Mark E. Brandt; Michael E. April; Colin Thomson
- Book ID
- 104580779
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 428 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0020-7608
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π SIMILAR VOLUMES
A stereoselective, chiral synthesis of the glyoxalase I inhibitor 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6trihydroxycyclohex-2-enone 1 (COTC) from a simple derivative of (-)-quinic acid is described.
The synthesis of two a-aminocyclopropanone hydrates is reported. These synthons could find biological applications by acting as transition-state analog inhibitors of hydrolytic enzymes, such as serine proteases.
## Abstract The pseudolactones **6** and **12** were prepared in a straightforward way from methyl Ξ±βDβglucopyranoside and methyl Ξ±βDβmannopyranoside, respectively. The pseudolactone **6** reacted with __tert__βbutyl lithioacetate to give the protected, trihydroxylated cyclohexenone carboxylate **7