dear all
can anyone help be in selectively protecting the e-amino group in lysine as I wish to perform acylation of a-amino group iin lysine .
You can selectively protect the e-amino group of lysine (e.g. with Boc or another carbamate protecting group) in the presence of an excess of Cu2+ (the alpha amino and carboxyl group form a bidentate ligand to the Cu2+). Please consult a couple of papers for exact reaction conditions.
Look at the procedure for compound 36, it's very straightforward.
http://onlinelibrary.wiley.com/doi/10.1002/psc.2968/pdf
In page 4 you can find the synthesis of our compound, I would still use the protection of the amine provided in the previous paper given it's simpler and this particular paper's objective is avoid metal catalysts, something that shoulnd't be a concern for you, and pH control is way easier to fail in comparison to Cu2+ chelation. Basically, I'd do the Boc protection according to the previous one and the acetylation according to this one.
http://pubs.acs.org/doi/suppl/10.1021/ol061098a/suppl_file/ol061098asi20060614_105459.pdf
Hi Friends Can you share the above papers again or in my e-mail "[email protected]" ...These links are not working i guess.
Many thanks.
Gaurav
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