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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: john007 on April 02, 2014, 02:18:29 AM

Title: Reducing disulfide to thiol in the presence of Quaternary amine
Post by: john007 on April 02, 2014, 02:18:29 AM

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.

Title: Re: Reducing disulfide to thiol in the presence of Quaternary amine
Post by: Babcock_Hall on April 03, 2014, 11:50:39 AM

Have you tried any reductions yet?

Title: Re: Reducing disulfide to thiol in the presence of Quaternary amine
Post by: john007 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?

Title: Re: Reducing disulfide to thiol in the presence of Quaternary amine
Post by: discodermolide on April 04, 2014, 05:19:19 AM

Try sodium borohydride.

Title: Re: Reducing disulfide to thiol in the presence of Quaternary amine
Post by: Babcock_Hall 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.