117626-00-3Relevant academic research and scientific papers
Synthesis of a novel N-hydroxypyrrolidine using enzyme catalysed asymmetric carbon-carbon bond synthesis
Humphrey, Andrew J.,Parsons, Simon F.,Smith, Mark E. B.,Turner, Nicholas J.
, p. 4481 - 4485 (2000)
N-Hydroxypyrrolidine 5 has been prepared in nine steps starting from 3- O-benzylglyceraldehyde 13. The synthetic route employs Escherichia coli transketolase mediated C-C bond synthesis to establish the absolute stereochemistry and a subsequent ring contraction of a 1,2-oxazine 17 to provide the N-hydroxypyrrolidine nucleus. (C) 2000 Elsevier Science Ltd.
Structure-guided redesign of d-fructose-6-phosphate aldolase from E. coli: Remarkable activity and selectivity towards acceptor substrates by two-point mutation
Gutierrez, Mariana,Parella, Teodor,Joglar, Jesus,Bujons, Jordi,Clapes, Pere
supporting information; experimental part, p. 5762 - 5764 (2011/07/08)
Structure-guided re-design of the acceptor binding site of d-fructose-6-phosphate aldolase from E. coli leads to the construction of FSA A129S/A165G double mutant with an activity between 5- to >900-fold higher than that of wild-type towards N-Cbz-aminoal
D-fructose-6-phosphate aldolase in organic synthesis: Cascade chemical-enzymatic preparation of sugar-relafed polyhydroxylated compounds
Concia, Alda Lisa,Lozano, Caries,Castillo, Jose A.,Parella, Teodor,Joglar, Jesus,Clapes, Pere
experimental part, p. 3808 - 3816 (2010/01/16)
Novel aldol addition reactions of dihydroxyacetone (DHA) and hydroxyacetone (HA) to a variety of aldehydes catalyzed by D-fructose-6-phosphate aldolase (FSA) are presented. In a chemical-enzymatic cascade reaction approach, 1-deoxynojirimycin and 1-deoxymannojirimycin were synthesized starting from (R)- and (S)-3-(N-Cbz-amino)-2-hydroxypropanal, respectively. Furthermore, 1,4-dideoxy1,4-imino-D-arabinitol and 1,4,5-trideoxy-1,4-imino-D-arabinitol were prepared from N-Cbz-glycinal, 1 -Deoxy-D-xylulose was also synthesized by using HA as the donor and either 2-benzyloxyethanal or 2-hydroxyethanal as acceptors. In both cases the enzymatic aldol addition reaction was fully stereoselective, but with 2-hydroxyethanal 17% of the epimeric product at C2, 1-deoxy-D-erythro-2-pentulose, was observed due to enolization/epimerization during the isolation steps. It was also observed that D-(-)-threose is a good acceptor substrate for FSA, opening new synthetic possibilities for the preparation of important novel complex carbohydrate-related compounds from aldoses. To illustrate this, 1-deoxy-D-ido-hept-2-ulose was obtained stereoselectively by the addition of HA to D-(-)-threose, catalyzed by FSA. It was found that the reaction performance depended strongly on the donor substrate, HA being the one that gave the best conversions to the aldol adduct. The examples presented in this work show the valuable synthetic potential of FSA for the construction of chiral complex polyhydroxylated sugar-type structures.
Transketolase from Escherichia coli: A practical procedure for using the biocatalyst for asymmetric carbon-carbon bond synthesis
Morris, K. Gail,Smith, Mark E.B.,Turner, Nicholas J.,Lilly, Malcolm D.,Mitra, Robin K.,Woodley, John M.
, p. 2185 - 2188 (2007/10/03)
A practical procedure is reported for the use of the enzyme transketolase, from Escherichia coli, for asymmetric carbon-carbon bond synthesis. The reactions with the biocatalyst are conveniently carried out, on a gram scale, in unbuffered aqueous media by employing a pH autotitrator. An improved large scale synthesis of hydroxypyruvate is also reported.
Preparation of optically pure L-2-hydroxyaldehydes with yeast transketolase
Effenberger, Franz,Null, Volker,Ziegler, Thomas
, p. 5157 - 5160 (2007/10/02)
L-2-Hydroxyaldehydes L-3 with a great variety of substituents in 3-position are obtained in good chemical and excellent optical yields by kinetic resolution in the transketolase-catalyzed reaction of racemic 2-hydroxyaldehydes with lithium hydroxypyruvate
