Skip to main content
placeholder image

Glycosylation and functionalization of native amino acids with azido uronic acids

Journal Article


Abstract


  • Bifunctional, acetyl-protected, azido glucuronic and galacturonic acid derivatives were coupled via the carboxylic acid moiety to amine- and hydroxyl-containing side chains of the natural amino acids lysine and serine or via the N-terminus of the amino acids leucine, methionine and glutamine. The glycosylated amino acids were then functionalized via the free azido moiety to produce the corresponding anomeric triazole derivatives. This approach enables the dual glycosylation and functionalization of a range of native amino acids in high yields.

Publication Date


  • 2015

Citation


  • Cara, C. J. & Skropeta, D. (2015). Glycosylation and functionalization of native amino acids with azido uronic acids. Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 71 (49), 9357-9365.

Scopus Eid


  • 2-s2.0-84947583823

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3456

Number Of Pages


  • 8

Start Page


  • 9357

End Page


  • 9365

Volume


  • 71

Issue


  • 49

Abstract


  • Bifunctional, acetyl-protected, azido glucuronic and galacturonic acid derivatives were coupled via the carboxylic acid moiety to amine- and hydroxyl-containing side chains of the natural amino acids lysine and serine or via the N-terminus of the amino acids leucine, methionine and glutamine. The glycosylated amino acids were then functionalized via the free azido moiety to produce the corresponding anomeric triazole derivatives. This approach enables the dual glycosylation and functionalization of a range of native amino acids in high yields.

Publication Date


  • 2015

Citation


  • Cara, C. J. & Skropeta, D. (2015). Glycosylation and functionalization of native amino acids with azido uronic acids. Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 71 (49), 9357-9365.

Scopus Eid


  • 2-s2.0-84947583823

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3456

Number Of Pages


  • 8

Start Page


  • 9357

End Page


  • 9365

Volume


  • 71

Issue


  • 49