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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: Oyailke on May 07, 2016, 04:09:12 AM

Title: Deprotection of Fmoc group in solution phase
Post by: Oyailke on May 07, 2016, 04:09:12 AM

I have synthesized a peptide amphiphile with 17 amino acids. the last of the amino group is protected with Fmoc group and I want to remove it in solution phase. It is a negatively charged peptide and soluble in basic pH in water. Solubility in the most of organic solvents is very low. Amino acids have no protecting groups on them since I remove the peptide from resin with TFA cleavage. Do you have any suggestions?

Title: Re: Deprotection of Fmoc group in solution phase
Post by: kriggy on May 07, 2016, 07:49:47 AM

I think classic protocol is to deprotect with piperidine. Not sure if it will work in water but dont see reason why not (althought we usualy do that in organic solvents like DCM)

Title: Re: Deprotection of Fmoc group in solution phase
Post by: Dan on May 07, 2016, 09:07:10 AM

You can use DMF if it will dissolve in that. Otherwise it might be better to cleave the Fmoc before TFA cleavage from the resin.