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Deprotection of Nin-Formyl Group on Tryptophan by Application of New Reagent, 1,2-dimethylethylendiamine in Aqueous Solution

  • Takenao Odagami
  • Yuji Kogami
  • Hiroyuki Kouji
  • Yuko Tsuda
  • Yoshio Okada
Part of the Advances in Experimental Medicine and Biology book series (volume 611)

Introduction

In peptide synthesis, choosing side chain protection is one of the most important events. The Trp(Nin-For) derivative is widely used to overcome two main side-reactions occurring with Trp residue in the Boc chemistry. One problem is acid catalyzed oxidation or dimerization of the indole moiety during synthesis. The other is alkylation of the indole ring by t-butyl cation and t-butyl trifluoroacetate generated during cleavage.To date, a number of Nin-For deprotection procedures have been developed, including low-high HF treatment [1]. However, this method involves treatment of large amount of stench reagent (dimethyl sulfide) and use of special equipment. On the other hand, the Nin-For group can be removed in a weak alkaline medium, such as 1.0 M NH2OH[2] or 1.0 M NaHCO3[3]. Additionally, the Nin-For group can be cleaved by dissolving Trp(Nin-For) in DMF containing a 20–30 fold molar excess of hydrazine hydrate[4]. However, these procedures require application with excess...

Keywords

Hydrazine Hydrate Dimethyl Sulfide Formyl Group Indole Moiety Alkaline Reagent 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgments

The authors gratefully acknowledge Dr. Kiyoshi Ogawa at the Asahi Kasei Pharma Corp. for helpful analysis of RP-HPLC, LC/MS and LC/MS/MS.

References

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Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Takenao Odagami
    • 1
  • Yuji Kogami
    • 1
  • Hiroyuki Kouji
    • 1
  • Yuko Tsuda
    • 2
    • 3
  • Yoshio Okada
    • 2
    • 3
  1. 1.Research InstitutePRISM Bio LabIzunokunishiJapan
  2. 2.Faculty of Pharmaceutical Sciences, The Graduate School of Food and Medicinal SciencesKobe Gakuin UniversityKobeJapan
  3. 3.The Graduate School of Food and Medicinal SciencesKobe Gakuin UniversityKobeJapan

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