77796-20-4Relevant articles and documents
Simultaneous engineering of an enzyme's entrance tunnel and active site: The case of monoamine oxidase MAO-N
Li, Guangyue,Yao, Peiyuan,Gong, Rui,Li, Jinlong,Liu, Pi,Lonsdale, Richard,Wu, Qiaqing,Lin, Jianping,Zhu, Dunming,Reetz, Manfred T.
, p. 4093 - 4099 (2017/07/10)
A new directed evolution approach is presented to enhance the activity of an enzyme and to manipulate stereoselectivity by focusing iterative saturation mutagenesis (ISM) simultaneously on residues lining the entrance tunnel and the binding pocket. This combined mutagenesis strategy was applied successfully to the monoamine oxidase from Aspergillus Niger (MAO-N) in the reaction of sterically demanding substrates which are of interest in the synthesis of chiral pharmaceuticals based on the benzo-piperidine scaffold. Reversal of enantioselectivity of Turner-type deracemization was achieved in the synthesis of (S)-1,2,3,4-tetrahydro-1-methyl-isoquinoline, (S)-1,2,3,4-tetrahydro-1-ethylisoquinoline and (S)-1,2,3,4-tetrahydro-1-isopropylisoquinoline. Extensive molecular dynamics simulations indicate that the altered catalytic profile is due to increased hydrophobicity of the entrance tunnel acting in concert with the altered shape of the binding pocket.
4,5-Dihydrothiazoline - A new protecting and activating group for generation of α-aminocarbanions of secondary amines
Singh, Kamal Nain,Singh, Paramjit,Kaur, Amarjit
, p. 3339 - 3343 (2007/10/03)
4,5-Dihydrothiazoline has been successfully used as a protecting and activating group for synthesis of various 1-substituted 1,2,3,4- tetrahydroisoquinolines via a lithiation-electrophillic substitution reaction sequence. Copyright Taylor & Francis Group, LLC.
Free-Radical Chemistry of Imines
Tomaszewski, Miroslaw J.,Warkentin, John,Werstiuk, Nick H.
, p. 291 - 322 (2007/10/02)
Aryl radicals bearing an aldimino functional group as part of an ortho substituent cyclized by addition to C and/or N of the imino group.When the choice was between 5-exo closure to C and 6-endo closure to N, the former predominated.However, 6-endo closure to C predominated over 5-exo cyclization to N in isomeric imines.Absolute values of cyclization rate constants were determined and an explanation for the unusual 6-endo preference is offered.Chiral induction in 6-endo cyclization to C of an aldimine from D-glyceraldehyde acetonide was observed, and its sense was determined.