Synthesis of all stereoisomers of 3-hydroxypipecolic acid and 3-hydroxy-4,5-dehydropipecolic acid and their evaluation as glycosidase inhibitors

Chiaki Ohara; Ryouko Takahashi; Tatsunori Miyagawa; Yuichi Yoshimura; Atsushi Kato; Isao Adachi; Hiroki Takahata

doi:10.1016/j.bmcl.2008.02.028

Synthesis of all stereoisomers of 3-hydroxypipecolic acid and 3-hydroxy-4,5-dehydropipecolic acid and their evaluation as glycosidase inhibitors

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1810-3. doi: 10.1016/j.bmcl.2008.02.028. Epub 2008 Feb 14.

Authors

Chiaki Ohara¹, Ryouko Takahashi, Tatsunori Miyagawa, Yuichi Yoshimura, Atsushi Kato, Isao Adachi, Hiroki Takahata

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.

PMID: 18296050
DOI: 10.1016/j.bmcl.2008.02.028

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylglucosaminidase / antagonists & inhibitors*
Animals
Cattle
Chickens
Chromatography, High Pressure Liquid
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / pharmacology*
Escherichia coli / enzymology
Glucuronidase / antagonists & inhibitors*
Humans
Kidney / enzymology
Liver / enzymology
Mass Spectrometry
Pipecolic Acids / chemical synthesis*
Pipecolic Acids / pharmacology*
Placenta / enzymology
Stereoisomerism
alpha-N-Acetylgalactosaminidase / antagonists & inhibitors*

Substances

3-hydroxy-4,5-dehydropipecolic acid
3-hydroxypipecolic acid
Enzyme Inhibitors
Pipecolic Acids
Glucuronidase
alpha-N-Acetylgalactosaminidase
Acetylglucosaminidase