N5-Phosphonoacetyl-l-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae

Brad Johnson; Rachel Steadman; Krista D. Patefield; Jeffrey J. Bunker; Audrey L. Atkin; Patrick Dussault

doi:10.1016/j.bmcl.2011.02.081

N⁵-Phosphonoacetyl-l-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae

Brad Johnson, Rachel Steadman, Krista D. Patefield, Jeffrey J. Bunker, Audrey L. Atkin, Patrick Dussault

Chemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

A scalable four-step synthesis of the ornithine transcarbamylase inhibitor N⁵-phosphonoacetyl-l-ornithine (PALO) is achieved through boroxazolidinone protection of ornithine. Investigations in the model organism Saccharomyces cerevisiae found that, in contrast to a previous report, PALO did not influence growth rate or expression of genes involved in arginine metabolism.

Original language	English (US)
Pages (from-to)	2351-2353
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2011.02.081
State	Published - Apr 15 2011

Keywords

Arginine biosynthesis
Ornithine transcarbamylase
PALO
Saccharomyces cerevisiae

ASJC Scopus subject areas

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

Access to Document

10.1016/j.bmcl.2011.02.081

Cite this

Johnson, B., Steadman, R., Patefield, K. D., Bunker, J. J., Atkin, A. L., & Dussault, P. (2011). N⁵-Phosphonoacetyl-l-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae. Bioorganic and Medicinal Chemistry Letters, 21(8), 2351-2353. https://doi.org/10.1016/j.bmcl.2011.02.081

N⁵-Phosphonoacetyl-l-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae. / Johnson, Brad; Steadman, Rachel; Patefield, Krista D. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 8, 15.04.2011, p. 2351-2353.

Research output: Contribution to journal › Article › peer-review

Johnson, B, Steadman, R, Patefield, KD, Bunker, JJ, Atkin, AL & Dussault, P 2011, 'N⁵-Phosphonoacetyl-l-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae', Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 8, pp. 2351-2353. https://doi.org/10.1016/j.bmcl.2011.02.081

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abstract = "A scalable four-step synthesis of the ornithine transcarbamylase inhibitor N5-phosphonoacetyl-l-ornithine (PALO) is achieved through boroxazolidinone protection of ornithine. Investigations in the model organism Saccharomyces cerevisiae found that, in contrast to a previous report, PALO did not influence growth rate or expression of genes involved in arginine metabolism.",

keywords = "Arginine biosynthesis, Ornithine transcarbamylase, PALO, Saccharomyces cerevisiae",

author = "Brad Johnson and Rachel Steadman and Patefield, {Krista D.} and Bunker, {Jeffrey J.} and Atkin, {Audrey L.} and Patrick Dussault",

note = "Funding Information: We thank Dr. Steven Fields (Dow Agro, Indianapolis, IN) for useful discussions and a preprint describing investigations of PALO synthesis. Support was provided by the University of Nebraska-Lincoln Research Council and by NIH INBRE scholarships to R.S. and J.B. This work was conducted in part, in facilities remodeled with support from the NIH ( RR0116544-01 ) and employing instrumentation purchased with NSF support (MRI 0079750 and CHE 0091975). ",

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