Any Chemists Out There?

[BadThad]

I'm looking for a chromophoric chemical that will react instantly (hoping for) with primary, secondary and tertiary amines to form a compound that I can detect using HPLC/UV. The amines are generally small like monoethanolamine, diethanolamine, isopropylamine, etc. Organic chemistry is not my strong suit.

Edit - Obviously, the end product must be water soluble for reverse-phase HPLC.

 

[Soccerman06]

:beer:

 

[Gibsons]

Just a guess: diethyl pyrocarbonate. It reacts with uh... some kind of amine (primary? It reacts with tris base).

IIRC, it's very fast.


edit (I was bored):
-------------
Merck Manual as pyrocarbonic acid diethyl ester.
C2H5OOCOCOOC2H5
Use: gentle esterifying agent.


It's used a great deal in molecular biology (usually just called DEPC) for treating aqueous solutions to remove RNAse contamination. If memory serves, it adds a group (ethyl of some sort, but maybe through an O, which would be something else nomenclature wise) to Histidine residues. It can't be used in Tris buffered solutions however, as it reacts with tris much faster than it reacts with histidine. Tris is actually tris(hydroxymethyl) amino methane. So it's a primary amine.

But I've no idea if depc reacts with secondary or tertiary amines. 🙁

 

[Monkeytool]

macrocyclic phenol-formaldehyde tetramer or Calixarene its also called
http://en.wikipedia.org/wiki/Calixarene
I believe the macro molecules to be pretty fast reacting and will certainly react with your amines, may also interact with other substrates and depending on your medium it may not work but you could probably discern the reaction visually an easily with some simple chromatography.
I am assuming you are looking to end up with some like Chromogenic Diethanol Calixarene
hope this helps, I did some subunit binding work back in college and we used several Macromolecules to do chromogenic bindings using amine groups, so this is one I remember, I know there were a lot more. If you want I could pick my brain further.

 

[BadThad]

Originally posted by: Gibsons
Just a guess: diethyl pyrocarbonate. It reacts with uh... some kind of amine (primary? It reacts with tris base).

IIRC, it's very fast.


edit (I was bored):
-------------
Merck Manual as pyrocarbonic acid diethyl ester.
C2H5OOCOCOOC2H5
Use: gentle esterifying agent.


It's used a great deal in molecular biology (usually just called DEPC) for treating aqueous solutions to remove RNAse contamination. If memory serves, it adds a group (ethyl of some sort, but maybe through an O, which would be something else nomenclature wise) to Histidine residues. It can't be used in Tris buffered solutions however, as it reacts with tris much faster than it reacts with histidine. Tris is actually tris(hydroxymethyl) amino methane. So it's a primary amine.

But I've no idea if depc reacts with secondary or tertiary amines. 🙁

The resultant reaction product will not be chromophoric, it may have a little absorbance at around 190 nm due to the double bonds, but that is far too weak for my purposes. I need a pretty strong chromophore (phenyl rings are nice) and enough MW to permit separtion using reverse-phase HPLC.

 

[BadThad]

Originally posted by: Monkeytool
macrocyclic phenol-formaldehyde tetramer or Calixarene its also called
http://en.wikipedia.org/wiki/Calixarene
I believe the macro molecules to be pretty fast reacting and will certainly react with your amines, may also interact with other substrates and depending on your medium it may not work but you could probably discern the reaction visually an easily with some simple chromatography.
I am assuming you are looking to end up with some like Chromogenic Diethanol Calixarene
hope this helps, I did some subunit binding work back in college and we used several Macromolecules to do chromogenic bindings using amine groups, so this is one I remember, I know there were a lot more. If you want I could pick my brain further.

Wow....that is a giant molecule, definately will have a ton of UV/Vis absorbance. My only concern, it doesn't look polar enough to be water soluble. Not sure I see how it would react with an amine based on the structure.

I'm looking at some other possibilities: ninhydrin, acylchlorides and acid anhydrides.

Please continue to "pick your brain", lol. I appreciate the input! 🙂

Thanks!

 

[BadThad]

Still looking bump!

 

[BadThad]

Not many chemists in the crowd, eh? 🙁

 

[sao123]

2 H2 + O2 -> 2 H2O