Synthesis of all stereoisomers of 3-hydroxypipecolic acid and 3-hydroxy-4,5-dehydropipecolic acid and their evaluation as glycosidase inhibitors.
A highly practicable synthesis of both enantiomers of 3-hydroxypipecolic acid derivatives 1, 2, 3, 4 is described. Screening of these molecules for glycosidase inhibition has been examined. Compound 3 was shown to be a potent inhibitor of beta-N-acetylglucosaminidase as well as Escherichia coli beta-glucuronidase.
Ohara
Chiaki
C
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
Takahashi
Ryouko
R
Miyagawa
Tatsunori
T
Yoshimura
Yuichi
Y
Kato
Atsushi
A
Adachi
Isao
I
Takahata
Hiroki
H
D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors*; D000818:Animals; D002417:Cattle; D002645:Chickens; D002851:Chromatography, High Pressure Liquid; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D004926:Escherichia coli / Q000201:enzymology; D005966:Glucuronidase / Q000037:antagonists & inhibitors*; D006801:Humans; D007668:Kidney / Q000201:enzymology; D008099:Liver / Q000201:enzymology; D013058:Mass Spectrometry; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D010920:Placenta / Q000201:enzymology; D013237:Stereoisomerism; D048809:alpha-N-Acetylgalactosaminidase / Q000037:antagonists & inhibitors*
C529305:3-hydroxy-4,5-dehydropipecolic acid; C529304:3-hydroxypipecolic acid; D004791:Enzyme Inhibitors; D010875:Pipecolic Acids; D005966:Glucuronidase; D048809:alpha-N-Acetylgalactosaminidase; D000118:Acetylglucosaminidase