Enzymatic syntheses of rare ketose 1-phosphates

Structure and Reaction Mechanism of l-Rhamnulose Kinase from Escherichia coli

“…Several of them have to rearrange on binding the divalent Mg 2C or Mn 2C required for catalysis. 34 The cation most likely binds between Asp10 and the b and g-phosphate groups in the active enzyme (see below). The phosphates are further stabilized by hydrogen bonds to amides and side-chains from the two b-hairpins around positions 13 and 259, as well as from Gly402 N ( Figure 4).…”

Die Dihydroxyaceton‐Einheit – ein nützlicher C3‐Baustein in der Organischen Synthese

“…[14,15] Darüber hinaus ermöglichen die beiden Enzyme l-Fuculose-1-phosphat-Aldolase (FucA) and lRhamnulose-1-phosphat-Aldolase (RhuA) eine effiziente kinetische Racematspaltung von 2-Hydroxyaldehyden. [16] Barbas III et al berichteten kürzlich über die direkte Aldolreaktion von DHA mit verschiedenen Aldehyden unter Verwendung von (S)-1-(2-Pyrrolidinylmethyl)pyrrolidin (13) als Katalysator in gepuffertem wässrigem Medium (Schema 4). [17] Dieser organokatalytische [18] [24, 25a, 26, 27] Das Problem bei DHA-Derivaten mit zwei unterschiedlichen Schutzgruppen liegt in der Regioselektivität, [24] doch für die Bildung von Borenolaten tritt dieses nicht mehr auf, falls man zu höher substituierten Analoga übergeht.…”

The Dihydroxyacetone Unit—A Versatile C3Building Block in Organic Synthesis

“…[14,15] Moreover, the enzymes l-fuculose-1-phosphate aldolase (FucA) and l-rhamnulose-1-phosphate aldolase (RhuA) can be employed for the efficient kinetic resolution of 2-hydroxyaldehydes. [16] Recently, Barbas III and co-workers reported a direct aldol reaction of DHA with different aldehydes in the presence of (S)-1-(2-pyrrolidinylmethyl)pyrrolidine (13) as the catalyst in a buffered aqueous medium (Scheme 4). [17] This organocatalytic [18] approach corresponds to a class I aldolase catalyzed reaction (that is, a reaction that proceeds via an enamine intermediate of DHA).…”