title: De novo chemoenzymatic synthesis of sialic acid.
abstract: A chemoenzymatic synthesis of sialic acid from inexpensive N-acetyl-D-glucosamine is described. In a three-step Wittig-protection-ozonolysis strategy manno-configured aldehydes are obtained. Treatment with oxaloacetate in the presence of macrophomate synthase affords the signature α-keto-γ-hydroxy acid moiety with high diastereoselectivity.
authors.affiliation: Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam-Golm, Germany.
authors.forename: Pierre
authors.initials: P
authors.lastname: Stallforth
authors.forename: Stefan
authors.initials: S
authors.lastname: Matthies
authors.forename: Alexander
authors.initials: A
authors.lastname: Adibekian
authors.forename: Dennis G
authors.initials: DG
authors.lastname: Gillingham
authors.forename: Donald
authors.initials: D
authors.lastname: Hilvert
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D002236:Carbohydrate Conformation; D009097:Multienzyme Complexes / Q000737:chemistry / Q000378:metabolism*; D019158:N-Acetylneuraminic Acid / Q000096:biosynthesis* / Q000737:chemistry
chemical_list: D009097:Multienzyme Complexes; C408144:macrophomate synthase; D019158:N-Acetylneuraminic Acid