A Novel Synthesis of p-Nitrobenzylphosphonic Acid and Its Action on Alkaline Phosphatase

C. Michele Davis McGibony; Kevin J. Hand; R. Bryan Sears; Trianna R. McCall

doi:10.2174/157017808785982167

A Novel Synthesis of p-Nitrobenzylphosphonic Acid and Its Action on Alkaline Phosphatase

C. Michele Davis McGibony, Kevin J. Hand, R. Bryan Sears, Trianna R. McCall

Biochemistry, Chemistry & Physics

Georgia Southern University

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

Abstract

p-Nitrobenzylphosphonic acid was obtained via a nucleophilic substitution of nitrobenzyl bromide with trimethyl phosphite as opposed to nitration of benzylphosphonic acid. This compound is a competitive inhibitor of alkaline phosphatase (K_I ∼ 125 μM) and has potential to inhibit a wide range of other phosphatases including serine/threonine phosphatases and tyrosine phosphatases.

Original language	American English
Journal	Letters in Organic Chemistry
Volume	5
DOIs	https://doi.org/10.2174/157017808785982167
State	Published - Jan 1 2008

Disciplines

Biochemistry

Keywords

Alkaline phosphatase
enzyme inhibition
nucleophilic substitution

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http://dx.doi.org/10.2174/157017808785982167

Cite this

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title = "A Novel Synthesis of p-Nitrobenzylphosphonic Acid and Its Action on Alkaline Phosphatase",

abstract = "p-Nitrobenzylphosphonic acid was obtained via a nucleophilic substitution of nitrobenzyl bromide with trimethyl phosphite as opposed to nitration of benzylphosphonic acid. This compound is a competitive inhibitor of alkaline phosphatase (KI ∼ 125 μM) and has potential to inhibit a wide range of other phosphatases including serine/threonine phosphatases and tyrosine phosphatases.",

keywords = "Alkaline phosphatase, enzyme inhibition, nucleophilic substitution",

author = "{Davis McGibony}, {C. Michele} and Hand, {Kevin J.} and Sears, {R. Bryan} and McCall, {Trianna R.}",

year = "2008",

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language = "American English",

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journal = "Letters in Organic Chemistry",

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T1 - A Novel Synthesis of p-Nitrobenzylphosphonic Acid and Its Action on Alkaline Phosphatase

AU - Davis McGibony, C. Michele

AU - Hand, Kevin J.

AU - Sears, R. Bryan

AU - McCall, Trianna R.

PY - 2008/1/1

Y1 - 2008/1/1

N2 - p-Nitrobenzylphosphonic acid was obtained via a nucleophilic substitution of nitrobenzyl bromide with trimethyl phosphite as opposed to nitration of benzylphosphonic acid. This compound is a competitive inhibitor of alkaline phosphatase (KI ∼ 125 μM) and has potential to inhibit a wide range of other phosphatases including serine/threonine phosphatases and tyrosine phosphatases.

AB - p-Nitrobenzylphosphonic acid was obtained via a nucleophilic substitution of nitrobenzyl bromide with trimethyl phosphite as opposed to nitration of benzylphosphonic acid. This compound is a competitive inhibitor of alkaline phosphatase (KI ∼ 125 μM) and has potential to inhibit a wide range of other phosphatases including serine/threonine phosphatases and tyrosine phosphatases.

KW - Alkaline phosphatase

KW - enzyme inhibition

KW - nucleophilic substitution

UR - https://digitalcommons.georgiasouthern.edu/chem-facpubs/53

UR - http://dx.doi.org/10.2174/157017808785982167

U2 - 10.2174/157017808785982167

DO - 10.2174/157017808785982167

M3 - Article

SN - 1570-1786

VL - 5

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

ER -

A Novel Synthesis of p-Nitrobenzylphosphonic Acid and Its Action on Alkaline Phosphatase

Abstract

Disciplines

Keywords

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