A Nitro Sugar-Mediated Stereocontrolled Synthesis of beta(2)-Amino Acids: Synthesis of a Polyhydroxylated trans-2-Amino-cyclohexanecarboxylic Acid

作者：Otero Jose M^*; Fernandez Fernando; Estevez Juan C; Nash Robert; Estevez Ramon J

来源：European Journal of Organic Chemistry, 2012, (15): 2969-2979.

DOI：10.1002/ejoc.201200103

• Amino acids
• Carbohydrates
• Michael addition
• Protein engineering
• Peptidomimetics
• Inhibitors

The first stereocontrolled nitro sugar-mediated synthesis of polyhydroxylated beta-amino acids and their incorporation into peptides is described. The key steps of this approach are a Michael addition of the lithium salt of tris(phenylthio)methane (a carboxyl synthetic equivalent) to sugar nitro olefins, and the reduction of the nitro group to an amino group. Specifically, two glyceraldehyde-based beta-amino acids and a polyhydroxylated cyclohexyl beta-amino acid were prepared. The latter, which could act as a water-soluble mimic of the proline-glycine d-turn, was easily transformed into the corresponding 5-amino-6-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol, a novel amino-carbasugar. However, this did not show significant glycosidase inhibiting properties.

• 出版日期2012-5