Pivaloyloxymethyl
Encyclopedia
Pivaloyloxymethyl is a protecting group
used in organic synthesis
. The POM radical
has the formula (CH3)3C-CO-O-CH2.
The POM group is also sometimes used to produce prodrug
s. For example, the POM group can be attached to a negatively charged organophosphate
group(s) of a drug causing a neutralization of the negative charge, which can allow the drug to become more lipid soluble and thus more able to diffuse passively across cell membrane
s into cells. Upon entry into cells, the POM portion of the molecule can be removed by cellular processes resulting in release of active drug.
Clinically used prodrugs containing pivaloyloxymethyl groups include adefovir dipivoxil. Tenofovir disoproxil fumarate contains a very similar prodrug group.
Protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...
used in organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
. The POM radical
Radical (chemistry)
Radicals are atoms, molecules, or ions with unpaired electrons on an open shell configuration. Free radicals may have positive, negative, or zero charge...
has the formula (CH3)3C-CO-O-CH2.
The POM group is also sometimes used to produce prodrug
Prodrug
A prodrug is a pharmacological substance administered in an inactive form. Once administered, the prodrug is metabolised in vivo into an active metabolite, a process termed bioactivation. The rationale behind the use of a prodrug is generally for absorption, distribution, metabolism, and...
s. For example, the POM group can be attached to a negatively charged organophosphate
Organophosphate
An organophosphate is the general name for esters of phosphoric acid. Phosphates are probably the most pervasive organophosphorus compounds. Many of the most important biochemicals are organophosphates, including DNA and RNA as well as many cofactors that are essential for life...
group(s) of a drug causing a neutralization of the negative charge, which can allow the drug to become more lipid soluble and thus more able to diffuse passively across cell membrane
Cell membrane
The cell membrane or plasma membrane is a biological membrane that separates the interior of all cells from the outside environment. The cell membrane is selectively permeable to ions and organic molecules and controls the movement of substances in and out of cells. It basically protects the cell...
s into cells. Upon entry into cells, the POM portion of the molecule can be removed by cellular processes resulting in release of active drug.
Clinically used prodrugs containing pivaloyloxymethyl groups include adefovir dipivoxil. Tenofovir disoproxil fumarate contains a very similar prodrug group.