133039-03-9Relevant academic research and scientific papers
Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
Moreno, Carlos J.,Hernández, Karel,Charnok, Simon J.,Gittings, Samantha,Bolte, Michael,Joglar, Jesús,Bujons, Jordi,Parella, Teodor,Clapés, Pere
, p. 4660 - 4669 (2021/05/04)
Three enzymatic routes toward γ-hydroxy-α-amino acids by tandem aldol addition-transamination one-pot two-step reactions are reported. The approaches feature an enantioselective aldol addition of pyruvate to various nonaromatic aldehydes catalyzed by trans-o-hydroxybenzylidene pyruvate hydratase-aldolase (HBPA) from Pseudomonas putida. This affords chiral 4-hydroxy-2-oxo acids, which were subsequently enantioselectively aminated using S-selective transaminases. Three transamination processes were investigated involving different amine donors and transaminases: (i) l-Ala as an amine donor with pyruvate recycling, (ii) a benzylamine donor using benzaldehyde lyase from Pseudomonas fluorescens Biovar I (BAL) to transform the benzaldehyde formed into benzoin, minimizing equilibrium limitations, and (iii) l-Glu as an amine donor with a double cascade comprising branched-chain α-amino acid aminotransferase (BCAT) and aspartate amino transferase (AspAT), both from E. coli, using l-Asp as a substrate to regenerate l-Glu. The γ-hydroxy-α-amino acids thus obtained were transformed into chiral α-amino-γ-butyrolactones, structural motifs found in many biologically active compounds and valuable intermediates for the synthesis of pharmaceutical agents.
A Convergent Synthesis of the Macrocyclic Core of Cytotrienins: Application of RCM for Macrocyclization
Evano, Gwilherm,Schaus, Jennifer V.,Panek, James S.
, p. 525 - 528 (2007/10/03)
(Equation presented) The asymmetric synthesis of the fully elaborated macrocyclic core of cytotrienins A-D, potent apoptosis-inducing agents, is described. Synthetic highlights include the construction of the aniline bond using a copper-mediated amidation and the use of a ring-closing metathesis (RCM) reaction to efficiently install the (E,E,E)-triene and simultaneously construct the macrocyclic lactam.
The selective inhibition of phosphatases by natural toxins: The anhydride domain of tautomycin is not a primary factor in controlling PP1/PP2A selectivity
Liu, Wen,Sheppeck II, James E.,Colby, David A.,Huang, Hsien-Bin,Nairn, Angus C.,Chamberlin, A. Richard
, p. 1597 - 1600 (2007/10/03)
Analogues of the potent and moderately selective PP1/PP2A inhibitor tautomycin (TM) were prepared with modifications in the C1′-C7′ anhydride moiety. While all retain varying degrees of activity within a 3000-fold range of potencies, they also show remarkable constancy in their IC50 ratios, suggesting that the anhydride moiety is not critical in controlling the selectivity of inhibition.
A new, short and efficient synthesis of both enantiomers of carnitine
Bellamy,Bondoux,Dodey
, p. 7323 - 7326 (2007/10/02)
A short, efficient and enantioselective synthesis of both (R) and (S) enantiomers of carnitine is reported starting with (R) or (S) malic acid and involving a chemoselective reduction step.
