29640-04-8Relevant academic research and scientific papers
Characterization of three novel enzymes with imine reductase activity
Gand,Müller,Wardenga,H?hne
, p. 126 - 132 (2015/02/19)
Imine reductases (IRED) are promising catalysts for the synthesis of optically pure secondary cyclic amines. Three novel IREDs from Paenibacillus elgii B69, Streptomyces ipomoeae 91-03 and Pseudomonas putida KT2440 were identified by amino acid or structural similarity search, cloned and recombinantly expressed in E. coli and their substrate scope was investigated. Besides the acceptance of cyclic amines, also acyclic amines could be identified as substrates for all IREDs. For the IRED from P. putida, a crystal structure (PDB-code 3L6D) is available in the database, but the function of the protein was not investigated so far. This enzyme showed the highest apparent E-value of approximately Eapp = 52 for (R)-methylpyrrolidine of the IREDs investigated in this study. Thus, an excellent enantiomeric purity of >99% and 97% conversion was reached in a biocatalytic reaction using resting cells after 24 h. Interestingly, a histidine residue could be confirmed as a catalytic residue by mutagenesis, but the residue is placed one turn aside compared to the formally known position of the catalytic Asp187 of Streptomyces kanamyceticus IRED.
Geometry-selective synthesis of e or Z N -vinyl ureas (N -carbamoyl enamines)
Lefranc, Julien,Tetlow, Daniel J.,Donnard, Morgan,Minassi, Alberto,Galvez, Erik,Clayden, Jonathan
supporting information; experimental part, p. 296 - 299 (2011/03/22)
N-Vinyl ureas are emerging as a valuable class of compounds with both nucleophilic and electrophilic reactivity. They may be made by capturing the enamine tautomer of an imine with an isocyanate, a reaction which in general leads to the E isomer of the vi
Tandem β-alkylation-α-arylation of amines by carbolithiation and rearrangement of N -carbamoyl enamines (Vinyl Ureas)
Clayden, Jonathan,Donnard, Morgan,Lefranc, Julien,Minassi, Alberto,Tetlow, Daniel J.
supporting information; experimental part, p. 6624 - 6625 (2010/07/03)
Organolithiums add in an umpolung fashion to the β-carbon of N-carbamoyl enamines (N-vinyl ureas). The reaction proceeds with syn diastereospecificity and provides urea-stabilized, configurationally defined organolithiums. Facilitated by coordinating solv
Regiochemistry in aryl radical cyclisations (5-exo versus 6-endo) of N-vinylic 2-iodobenzamides
Ishibashi, Hiroyuki,Ohata, Kohei,Niihara, Michiyo,Sato, Tatsunori,Ikeda, Masazumi
, p. 547 - 554 (2007/10/03)
Bu3SnH-mediated aryl radical cyclisations of a range of N-vinylic 2-iodobenzamides 10 were examined. The enamides 10a-d gave exclusively the 5-exo cyclisation products 11a-d, whereas the enamides 10e,f having a phenyl substituent on the vinylic carbon ato
Synthesis of 3-Phenylisoquinolones by Reaction of Simple Pyrroline-2,3-diones with Benzyne. New Mechanistic Considerations
Cobas, Agustin,Guitian, Enrique,Castedo, Luis
, p. 3113 - 3117 (2007/10/02)
3-Phenylisoquinolones were obtained by cycloaddition of benzyne to 5-phenylpyrroline-2,3-diones.New mechanistic hypotheses for these transformations are discussed.
SYNTHESIS OF ARYLIMINES FROM N-SILYLAMIDES AND ARYLLITHIUM COMPOUNDS
Feringa, Ben L.,Jansen, F. G. A.
, p. 507 - 508 (2007/10/02)
Various arylimines were synthesized by the addition of N-silylated-N-alkyl- or N-aryl-amides to aryllithium compounds.
