chemical tetralinyl group

[kikothedog]

Hi guys, is there anyone here that can tell my how to introduce a tetralinyl group into my sample.

 

I have very little chemistry understanding so I have no idea which chemical solution to make up for this.

 

Thanks for any and all help.

 

Kiko

[hypervalent_iodine]

For your own safety and for the safety of others, you should not be attempting synthetic chemistry if you have no idea what you're doing.

[kikothedog]

I'm an immunologist working on therapeutic proteins.

 

I seem to do okay around all that chemical stuff we have in the lab without so far killing anyone, but really, thank you for the very unhelpful advise there!

[John Cuthber]

You just wrote off "don't hurt yourself and others" as "unhelpful advise".

Do you think that will have advanced your cause?

 

BTW, as written, your question has no real answer.

Edited October 14, 2013 by John Cuthber

[kikothedog]

Thanks for the reply, guess I'll just pass the issue on to the protein chemists to figure out.

[hypervalent_iodine]

That sounds like a wise decision.

[BabcockHall]

You need to provide more information, and then it may be possible to help. What is your sample, and what is your goal? What kind of side chain do you wish to modify? (etc.)

[kikothedog]

Hi BabcockHall

 

I am studying the bonding dynamics in several protein structures but my experiment is modifying several of the side chains causing additional conformational changes to my proteins.

 

There are already several chemical groups that have been used successfully to protect residues during process which are later removed from the sample. The PI on my work suggested the introduction of a tetralinyl group but I have never used this before and he provided no more information as to how to go about this.

 

If you have any suggestions they would be most welcome. I have passed the info back to the protein guys but they can be touchy about their work ruined for my enjoyment.

 

Kiko

[BabcockHall]

The only reference to the use of this group with which I am familiar was in the context of peptide synthesis, as opposed to the chemical modification of proteins. That having been said, I have not searched carefully, either.

http://profiles.uonbi.ac.ke/ayusuf/publications/1-tetralinyl-group-asparagine-side-chain-protection-and-application-boc-solid-ph

[vampares]

Tetralin AKA

tetrahydronaphthalene
1,2,3,4-tetrahydronaphthalenyl

 

It is a hydrogenated naphthalene molecule (or the equivalent to one). The naphthalene retains its numbering assignments, so this this hydrogenated at carbon 1,2,3 and 4.

 

It will be added at the carbon 1 position.

 

There is the cyclization strategy and naphthalene strategy.

 

 

According to my book tetralin can be produced by adding {Na, ethanol, heat} to naphthalene. If you were able to place a leaving group on the naphthalene ring and use this reaction with out dropping the leaving group then you could use this in as a means of adding tetralinyl perhaps.

 

Hydrogenation of naphthalene will produce decalin.

 

A potential leaving group could be Br by Br2.

 

With asparagine this could create a amide with a stabilized group. The Boc group mentioned in the google search, t-butooxycarbonyl is used for the first amino acid. It is an amino blocking group. Because asparagine has an open nitrogen it also needs a blocking group permanently throughout synthesis because it would otherwise act as an available unchained nitrogen. Due to the nature of protein synthesis by chemical reagents this would otherwise create a very large mess.

 

Another way to add tetralinyl would be by cyclization. The reagents would be more expensive. Likely candidates would be involve a benzoid with an unsaturated chain and some other unsaturated alkene. The likelihood of hitting the oxygen is higher in situ.

 

Other methods could involve removing the nitrogen altogether and then replacing it later on. This is a very good option in my opinion because tetralinyl seems to be a rather tentative occupancy. I'm not sure which is worse the naphthelene or the tetralinyl. Nothing really takes up on nitrogen and I think not removing it is one of the headaches.

Edited November 12, 2013 by vampares