Bioreversible Protection for the Phospho Group: Chemical Stability and Bioactivation of Di(4-acetoxybenzyl) Methylphosphonate with Carboxyesterase

DOI: 10.1039/c39910000875

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 875 - 877 (1991)

Update date:2022-08-04

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Authors:

Freeman, Sally

Irwin, William J.

Mitchell, Antony G.

Nicholls, Dave

Thomson, William

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Article abstract of DOI:10.1039/c39910000875

In contrast to high chemical stability (t_1/2 55.4 h at 36.4 deg C), with porcine liver carboxyesterase the title compound 1 spontaneously decomposes first to the monoester 2 then to methylphosphonate, both reactions proceeding via the 4-hydroxybenzyl intermediates 3 and 4.

Full text of DOI:10.1039/c39910000875

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