- Eight-step synthesis of routiennocin
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Routiennocin is a member of a family of polycyclic pyrrole ether antibiotics that simultaneously uncouple oxidative phosphorylation and inhibit ATPase as a result of selective complexation of divalent metal ions. We describe a concise synthesis of routien
- Matsumotoa, Kenji,Kozmina, Sergey A.
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supporting information; experimental part
p. 557 - 560
(2009/04/11)
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- Nitrile biotransformations for the synthesis of highly enantioenriched β-hydroxy and β-amino acid and amide derivatives: A general and simple but powerful and efficient benzyl protection strategy to increase enantioselectivity of the amidase
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(Chemical Equation Presented) Biotransformations of a number of racemic β-hydroxy and β-amino nitrile derivatives were studied using Rhodococcus erythropolis AJ270, the nitrile hydratase and amidase-containing microbial whole cell catalyst, under very mild conditions. The overall enantioselectivity of nitrile biotransformations was governed predominantly by the amidase whose enantioselectivity was switched on remarkably by an O- and a N-benzyl protection group of the substrates. While biotransformations of β-hydroxy and β-amino alkanenitriles gave low yields of amide and acid products of very low enantiomeric purity, introduction of a simple benzyl protection group on the β-hydroxy and β-amino of nitrile substrates led to the formation of highly enantioenriched β-benzyloxy and β-benzylamino amides and acids in almost quantitative yield. The easy protection and deprotection operations, high chemical yield, and excellent enantioselectivity render the nitrile biotransformation a useful protocol in the synthesis of enantiopure β-hydroxy and β-amino acids.
- Ma, Da-You,Wang, De-Xian,Pan, Jie,Huang, Zhi-Tang,Wang, Mei-Xiang
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p. 4087 - 4091
(2008/09/20)
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- Dramatic enhancement of enantioselectivity of biotransformations of β-hydroxy nitriles using a simple O-benzyl protection/docking group
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Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst, the O-benzylated β-hydroxy alkanenitriles underwent remarkably high enantioselective biotransformations, whereas the biotransformations of free β-hydroxy alkanenitriles gave very low ena
- Ma, Da-You,Zheng, Qi-Yu,Wang, De-Xian,Wang, Mei-Xiang
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p. 3231 - 3234
(2007/10/03)
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