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Topic: Reducing disulfide to thiol in the presence of Quaternary amine  (Read 2230 times)

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Offline john007

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Hello,

I am wondering if anyone can give me suggestion I am trying to reduce a disulfide to a thiol headgroup in the presence of a quaternary amine tail group without destroying the tail group.

Offline Babcock_Hall

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Re: Reducing disulfide to thiol in the presence of Quaternary amine
« Reply #1 on: April 03, 2014, 11:50:39 AM »
Have you tried any reductions yet?

Offline john007

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Re: Reducing disulfide to thiol in the presence of Quaternary amine
« Reply #2 on: April 04, 2014, 03:05:42 AM »
I was thinking of using LiAlH4 but that would destroy my quaternary amine structure to a tertiary amine any other reduction method ideas?

Offline discodermolide

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Re: Reducing disulfide to thiol in the presence of Quaternary amine
« Reply #3 on: April 04, 2014, 05:19:19 AM »
Try sodium borohydride.
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Offline Babcock_Hall

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Re: Reducing disulfide to thiol in the presence of Quaternary amine
« Reply #4 on: April 04, 2014, 09:01:56 AM »
In biochemistry an excess of a thiol, such as 2-mercaptoethanol or dithiothreitol (DTT), is often used to reduce the disulfide bonds of proteins.  You would then need to remove the side product and unreacted thiol.  I have no reason to think that sodium borohydride would not work unless there are other functional groups present.  Occasionally phosphines such as TCEP (tris-carboxyethylphosphine?) are used to reduce disulfides when the pH would be too low for DTT to be effective.
« Last Edit: April 04, 2014, 10:09:46 AM by Babcock_Hall »

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