[john007]

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.

[Babcock_Hall]

Have you tried any reductions yet?

[john007]

I was thinking of using LiAlH4 but that would destroy my quaternary amine structure to a tertiary amine any other reduction method ideas?

[discodermolide]

Try sodium borohydride.

[Babcock_Hall]

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.