Deprotection of the indole (N(ind))-formyl (For) group on tryptophan employing a new reagent, N,N'-dimethylethylendiamine (DMEDA) in an aqueous solution

Takenao Odagami; Yuko Tsuda; Yuji Kogami; Hiroyuki Kouji; Yoshio Okada

doi:10.1248/cpb.57.211

Deprotection of the indole (N(ind))-formyl (For) group on tryptophan employing a new reagent, N,N'-dimethylethylendiamine (DMEDA) in an aqueous solution

Chem Pharm Bull (Tokyo). 2009 Feb;57(2):211-3. doi: 10.1248/cpb.57.211.

Authors

Takenao Odagami¹, Yuko Tsuda, Yuji Kogami, Hiroyuki Kouji, Yoshio Okada

Affiliation

¹ Research Institute, Midori-ku, Yokohama, Japan.

PMID: 19182415
DOI: 10.1248/cpb.57.211

Abstract

The deprotection of the indole (N(ind))-formyl (For) group on Trp was achieved in a 95% yield using N,N'-dimethylethylendiamine (DMEDA) (1.5, 2.0, 3.0 eq) in water at room temperature. A new reagent was successfully applied to the deprotection of a model peptide, H-Phe-Trp(N(ind)-For)-Lys-Tyr-OH, to give H-Phe-Trp-Lys-Tyr-OH in a 91% yield.

MeSH terms

Chromatography, High Pressure Liquid
Ethylenediamines / chemistry*
Formates / chemistry
Indicators and Reagents
Indoles / chemistry*
Peptides / chemical synthesis
Peptides / chemistry
Solutions / analysis
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Ultraviolet
Tryptophan / chemistry*
Water / analysis

Substances

Ethylenediamines
Formates
Indicators and Reagents
Indoles
Peptides
Solutions
Water
formic acid
dimethylethylenediamine
Tryptophan