A fluorescent substrate for carbon-phosphorus lyase: towards the pathway for organophosphonate metabolism in bacteria

TY - JOUR

T1 - A fluorescent substrate for carbon-phosphorus lyase: towards the pathway for organophosphonate metabolism in bacteria

AU - He, Shu-Mei

AU - Lou, Yan

AU - Hove-Jensen, Bjarne

AU - Zechel, David L.

PY - 2009

Y1 - 2009

N2 - Many species of bacteria can use naturally occurring organophosphonates as a source of metabolic phosphate by cleaving the carbon-phosphorus bond with a multi-enzyme pathway collectively called carbon-phosphorus lyase (CP-lyase). Very little is known about the fate of organophosphonates entering this pathway. In order to detect metabolic intermediates we have synthesized a fluorescently labelled organophosphonate and show that this is a viable substrate for the CP-lyase pathway in Escherichia coli and that the expected product of CP-bond cleavage is formed. The in vivo competence of one potential metabolic intermediate, 1-ethylphosphonate-a-d-ribofuranose, is also demonstrated.

AB - Many species of bacteria can use naturally occurring organophosphonates as a source of metabolic phosphate by cleaving the carbon-phosphorus bond with a multi-enzyme pathway collectively called carbon-phosphorus lyase (CP-lyase). Very little is known about the fate of organophosphonates entering this pathway. In order to detect metabolic intermediates we have synthesized a fluorescently labelled organophosphonate and show that this is a viable substrate for the CP-lyase pathway in Escherichia coli and that the expected product of CP-bond cleavage is formed. The in vivo competence of one potential metabolic intermediate, 1-ethylphosphonate-a-d-ribofuranose, is also demonstrated.

U2 - 10.1016/j.bmcl.2009.08.035

DO - 10.1016/j.bmcl.2009.08.035

M3 - Journal article

C2 - 19733071

SN - 0960-894X

VL - 19

SP - 5954

EP - 5957

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 20

ER -