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

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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.

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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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Authors and Affiliations

  1. Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore , 560 001, India

    Vommina V. Sureshbabu, Rao Venkataramanarao & H. P. Hemantha

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  1. Vommina V. Sureshbabu
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  2. Rao Venkataramanarao
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  3. H. P. Hemantha
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Correspondence to Vommina V. Sureshbabu.

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Sureshbabu, V.V., Venkataramanarao, R. & Hemantha, H.P. A Facile Synthesis of C-terminal Neoglycopeptides: Incorporation of Urea Moiety between Sugars and Peptides Employing Curtius Rearrangement. Int J Pept Res Ther 14, 34–40 (2008). https://doi.org/10.1007/s10989-007-9101-4

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  • DOI: https://doi.org/10.1007/s10989-007-9101-4

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