alpha-1,4-Galactosyltransferase-catalyzed glycosylation of sugar and lipid modified Leu-enkephalins

Simerska, Pavla, Christie, Michelle P., Goodwin, Daryn, Jen, Freda E.-C., Jennings, Michael P. and Toth, Istvan (2013) alpha-1,4-Galactosyltransferase-catalyzed glycosylation of sugar and lipid modified Leu-enkephalins. Journal of Molecular Catalysis B: Enzymatic, In Press, Accepted Manuscript 1-28. doi:10.1016/j.molcatb.2013.08.018

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Author Simerska, Pavla
Christie, Michelle P.
Goodwin, Daryn
Jen, Freda E.-C.
Jennings, Michael P.
Toth, Istvan
Title alpha-1,4-Galactosyltransferase-catalyzed glycosylation of sugar and lipid modified Leu-enkephalins
Formatted title
α-1,4-Galactosyltransferase-catalyzed glycosylation of sugar and lipid modified Leu-enkephalins
Journal name Journal of Molecular Catalysis B: Enzymatic   Check publisher's open access policy
ISSN 1381-1177
Publication date 2013-09-03
Year available 2013
Sub-type Article (original research)
DOI 10.1016/j.molcatb.2013.08.018
Open Access Status
Volume In Press, Accepted Manuscript
Start page 1
End page 28
Total pages 28
Place of publication Amsterdam, Netherlands
Publisher Elsevier
Collection year 2014
Language eng
Formatted abstract
• Sugar and lipid modified enkephalin peptides were chemically synthesized.
• LgtC galactosyltransferase catalyzed conversion of enkephalin derivatives.
• Galactosylated products were purified in 13-71% yields.
• 5% DMSO increased solubility and enzymatic conversion of lipidated enkephalins.
• LgtC displayed unexpectedly high substrate specificity towards galactosyl moieties.

Glycosylation of therapeutic peptides has been reported to improve delivery and targeting of various vaccines and drugs to specific cells/tissues. However, chemical synthesis of complex oligosaccharide derivatives via conventional methods can be challenging due to the need for several orthogonal hydroxyl group protections. Liposaccharyl galactosyltransferase C, a naturally occurring glycosyltransferase enzyme from Neisseria meningitidis, was found to have the ability to transfer a galactosyl moiety to glyco(lipo)peptides. An enzymatic glycosylation of Leu-enkephalin glyco(lipo)peptides was developed and optimized in this study in order to prepare pain regulating peptides with potentially improved central nervous system delivery.
Keyword Enzymatic synthesis
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Available online 3 September 2013

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Chemistry and Molecular Biosciences
School of Pharmacy Publications
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Citation counts: TR Web of Science Citation Count  Cited 4 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 4 times in Scopus Article | Citations
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Created: Mon, 02 Sep 2013, 15:19:45 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences