Document Detail

Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase.
MedLine Citation:
PMID:  9871533     Owner:  NLM     Status:  MEDLINE    
The cis-4,5-epoxide derivative of L-pipecolic acid (2S,4S,5R-epoxypipecolic acid, cis-3) was synthesized and found to serve as an excellent substrate for L-pipecolate oxidase (L-PO) and also to cause time-dependent, irreversible inactivation of the enzyme. Data are presented showing this compound is a mechanism-based inhibitor of L-PO, whereas 2S,3R,4S-epoxyproline acts as a reversible inhibitor.
B Ho; T M Zabriskie
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  8     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  1998 Apr 
Date Detail:
Created Date:  1999-01-27     Completed Date:  1999-01-27     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  739-44     Citation Subset:  IM    
College of Pharmacy, Oregon State University, Corvallis 97331-3507, USA.
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MeSH Terms
Drug Design
Enzyme Inhibitors / chemical synthesis,  chemistry,  pharmacology*
Epoxy Compounds / chemical synthesis,  chemistry,  pharmacology*
Molecular Structure
Oxidoreductases Acting on CH-NH Group Donors / antagonists & inhibitors*
Pipecolic Acids / chemical synthesis,  chemistry,  pharmacology*
Proline / analogs & derivatives*,  chemical synthesis,  chemistry,  pharmacology
Structure-Activity Relationship
Grant Support
Reg. No./Substance:
0/Enzyme Inhibitors; 0/Epoxy Compounds; 0/Pipecolic Acids; 147-85-3/Proline; EC 1.5.-/Oxidoreductases Acting on CH-NH Group Donors; EC dehydrogenase

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