[sumdumguy]

Suppose I activate a carboxyl group with a cross-linker like EDC. Now I cross-link my chemicals to amines (e.g. via NHS). And finally I want the un-reacted intermediate to go back to carboxyl groups. How do I de-activate these residues (not just quench the reaction but perfectly reverse the activation of unreacted intermediates)?

[sumdumguy]

Come on. Somebody here knows how to promote hydrolysis without doing drastic stuff (e.g. without changing pH beyond 6.5-7.5 range or raising temperature). I am just looking for some simple chemical means to achieve near 100% hydrolysis fast (a few seconds to minutes). Anybody?

[zsinger]

First off, your assumption that everything will be "perfect" is juvenile at best.  NOTHING ever is perfect in this science.  I really have no idea what your talking about, but since you must know, answer yourself.  Something tells me that there are MANY MANY members on this board which are far smarter than you and I, and have not answered your question for a reason.  Additionally, "sumdumguy" does not lend itself to a very knowledgable chemist.....what level are you at?
         -Zack

[sumdumguy]

I do not think you want to judge a poster based on their avatar name. They just might be serious researchers with many top level journal papers and a few letters behind their name. They may or may not be chemists of course. Or they may just be sumdumguy. Who knows, right? I would hope the board just responds to a carefully stated inquiry. I certainly hope a more mature response with some actual substance is forthcoming. Hydrolysis of carboxylate esters is so well-studied that I expected tons of optimization strategies by now.
As far as "perfect"... sigh. I would certainly appreciate a meaningful protocol with good yield efficiencies. Hydrolysis will happen on its own at a non-zero rate so if one is willing to wait a long time and perform many buffer exchanges then one should be able to get pretty close to 100% yield. This is not juvenile at all. The question is more about optimization strategies.

[sumdumguy]

Here is an example of a paper which shows the research in this area is on-going.
doi:10.1016/j.cep.2011.04.003

There is also some recent work on the effect of micellar structures on hydrolysis rates that I am aware of (e.g. doi:10.1016/j.jscs.2014.01.002).

This is just to illustrate that I am asking a serious question and I am hoping for a comprehensive review of the field or some unpublished but cute and effective strategies from someone with a thorough knowledge of this field.