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Topic: Phosphorothioester displacement/substitution  (Read 2176 times)

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Offline calim3ntry

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Phosphorothioester displacement/substitution
« on: April 26, 2013, 02:30:20 PM »
Hello,

I'm a molecular biologist, so my chemistry is a little lacking. Wondering if I could get some help here. Are there any reactions/conditions/catalysts, etc. that you can think of that would easily displace/substitute/hydrolyze a phosphorothioester bond?
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Offline Babcock_Hall

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Re: Phosphorothioester displacement/substitution
« Reply #1 on: April 27, 2013, 05:54:03 PM »
Do you mean a bond of the type, P-S-C in which the sulfur replaces the bridging oxygen of the ester (this used to be called a phosphorothiolate linkage)?  Or do you mean a functional group in which the sulfur has replaced a nonbridging oxygen atom?  The conditions will be different.
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Offline Babcock_Hall

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Re: Phosphorothioester displacement/substitution
« Reply #2 on: April 30, 2013, 09:18:48 AM »
Phosphorothiolate linkages are quite susceptible to mild acid hydrolysis, reaching a maximum rate around pH 3.
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