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

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...

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Bibliographic Details
Published in:International journal of peptide research and therapeutics 2008-03, Vol.14 (1), p.34-40
Main Authors: Sureshbabu, Vommina V., Venkataramanarao, Rao, Hemantha, H. P.
Format: Article
Language:English
Subjects:
Animal Anatomy
Biochemistry
Biomedical and Life Sciences
Biophysics
Chemical synthesis
Histology
Life Sciences
Molecular Medicine
Morphology
Peptides
Pharmaceutical Sciences/Technology
Pharmacology/Toxicology
Polymer Sciences
Short Communication
Solvents
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Summary: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 1 H NMR and mass spectroscopy.
ISSN:1573-3149
1573-3904
DOI:10.1007/s10989-007-9101-4