638189-46-5Relevant articles and documents
Complete Switch of Reaction Specificity of an Aldolase by Directed Evolution In Vitro: Synthesis of Generic Aliphatic Aldol Products
Junker, Sebastian,Roldan, Raquel,Joosten, Henk-Jan,Clapés, Pere,Fessner, Wolf-Dieter
, p. 10153 - 10157 (2018/07/31)
A structure-guided engineering of fructose-6-phosphate aldolase was performed to expand its substrate promiscuity toward aliphatic nucleophiles, that is, unsubstituted alkanones and alkanals. A “smart” combinatorial library was created targeting residues D6, T26, and N28, which form a binding pocket around the nucleophilic carbon atom. Double-selectivity screening was executed by high-performance TLC that allowed simultaneous determination of total activity as well as a preference for acetone versus propanal as competing nucleophiles. D6 turned out to be the key residue that enabled activity with non-hydroxylated nucleophiles. Altogether 25 single- and double-site variants (D6X and D6X/T26X) were discovered that show useful synthetic activity and a varying preference for ketone or aldehyde as the aldol nucleophiles. Remarkably, all of the novel variants had completely lost their native activity for cleavage of fructose 6-phosphate.
Direct asymmetric aldol reactions in aqueous media catalyzed by a β-cyclodextrin-proline conjugate with a urea linker
Liu, Kegang,Zhang, Guoqi
supporting information, p. 243 - 246 (2015/02/02)
Covalently attaching proline to β-CD through a urea linkage resulted in the synthesis of a water-soluble chiral organocatalyst 1 in high yield. Catalytic asymmetric aldol condensations between aldehydes and acetone were carried out under water-containing
Catalytic asymmetric hydroperoxidation of α,β-unsaturated ketones: An approach to enantiopure peroxyhemiketals, epoxides, and aldols
Reisinger, Corinna M.,Wang, Xingwang,List, Benjamin
supporting information; experimental part, p. 8112 - 8115 (2009/04/13)
(Chemical Equation Presented) Efficient, selective: The primary amine salt 1 derived from quinine efficiently catalyzes the highly enantioselective hydroperoxidation of α,β-unsaturated ketones furnishing stable and isolable cyclic peroxyhemiketals in enan