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A Facile Synthesis of C-terminal Neoglycopeptides: Incorporation of Urea Moiety between Sugars and Peptides Employing Curtius Rearrangement

  • Vommina V. Sureshbabu
  • Rao Venkataramanarao
  • H. P. Hemantha
Short Communication

Abstract

Incorporation of urea moiety in the synthesis of C-terminal neoglycopeptides has been demonstrated through the reaction between suitably protected glycosylamine and Fmoc-peptidyl isocyanates or carbamates. Curtius rearrangement has been made use off for the conversion of peptidyl acid azides in to corresponding isocyanates. The resulting C-terminal neoglycopeptidylureas have been isolated as stable solids which are fully characterized by 1H NMR and mass spectroscopy.

Keywords

Curtius rearrangement neoglycopeptides glycosylamine ureido group Fmoc-peptidyl isocyanates 

Notes

Acknowledgements

We thank University Grants Commission, New Delhi, Govt. of India for financial assistance. R. V. R. Rao thanks the CSIR, New Delhi, Govt. of India for the award of fellowship.

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Vommina V. Sureshbabu
    • 1
  • Rao Venkataramanarao
    • 1
  • H. P. Hemantha
    • 1
  1. 1.Department of Studies in Chemistry, Central College CampusBangalore UniversityBangalore India

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