Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases.

@article{Yoshimura2008SynthesisOB,
  title={Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases.},
  author={Y. Yoshimura and Chiaki Ohara and T. Imahori and Yukako Saito and A. Kato and Saori Miyauchi and I. Adachi and H. Takahata},
  journal={Bioorganic \& medicinal chemistry},
  year={2008},
  volume={16 17},
  pages={
          8273-86
        }
}
We have synthesized 3-hydroxy- and 3,4,5-trihydroxypipecolic acid derivatives corresponding to 5-aza derivatives of uronic acids and evaluated their inhibitory activities against various glycosidases including beta-glucuronidase. Compounds 4 and 5 were chosen as common intermediates for the synthesis of 3,4,5-trihydroxypipecolic acids and 3-hydroxypipecolic acids as well as for 3-hydroxybaikiain, a unique natural product isolated from a toxic mushroom. Cross aldol reaction of N-Boc-allylglycine… Expand
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