Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase

Bin Ho; T. Mark Zabriskie

doi:10.1016/S0960-894X(98)00106-1

Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase

Bin Ho, T. Mark Zabriskie

Academic Affairs

Research output: Contribution to journal › Article

28 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	739-744
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	8
Issue number	7
DOIs	https://doi.org/10.1016/S0960-894X(98)00106-1
State	Published - Apr 7 1998

Fingerprint

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Cite this

Ho, B., & Zabriskie, T. M. (1998). Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase. Bioorganic and Medicinal Chemistry Letters, 8(7), 739-744. https://doi.org/10.1016/S0960-894X(98)00106-1

@article{34cad109e2984b73b464671791e7b9c5,

title = "Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase",

abstract = "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.",

author = "Bin Ho and Zabriskie, {T. Mark}",

year = "1998",

month = apr

day = "7",

doi = "10.1016/S0960-894X(98)00106-1",

language = "English (US)",

volume = "8",

pages = "739--744",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "7",

}

TY - JOUR

T1 - Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase

AU - Ho, Bin

AU - Zabriskie, T. Mark

PY - 1998/4/7

Y1 - 1998/4/7

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0032492704&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032492704&partnerID=8YFLogxK

U2 - 10.1016/S0960-894X(98)00106-1

DO - 10.1016/S0960-894X(98)00106-1

M3 - Article

C2 - 9871533

AN - SCOPUS:0032492704

VL - 8

SP - 739

EP - 744

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 7

ER -

Access to Document

10.1016/S0960-894X(98)00106-1