Proline organocatalysis as a new tool for the asymmetric synthesis of ulosonic acid precursors.
PEP and aldolase mimicry is the key for a direct organocatalytic entry to precursors of ulosonic acids, biomolecules of enormous importance in biology, chemistry and medicine; in the key aldol reaction the dimethylacetal of pyruvic aldehyde is used as phosphoenolpyruvate (PEP) equivalent and the amino acid proline functions as an organocatalyst, imitating the enzyme.
Enders
Dieter
D
Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, Aachen, 52074, Germany. enders@rwth-aachen.de
Gasperi
Tecla
T
D000080:Acetals / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D011765:Pyruvaldehyde / Q000737:chemistry; D012794:Sialic Acids / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
D000080:Acetals; D000447:Aldehydes; D012794:Sialic Acids; D013400:Sugar Acids; D011765:Pyruvaldehyde; D011392:Proline