Chemo-enzymatic synthesis of a glycosylated peptide containing a complex N-glycan based on unprotected oligosaccharides by using DMT-MM and Endo-M

Glycoconjugate Journal
Yusuke TomabechiKenji Yamamoto

Abstract

For chemo-enzymatic synthesis of a glycosylated peptide, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was used for the synthesis of a N-acetylglucosaminyl peptide and a pseudoglycopeptide by solid-phase peptide synthesis without the requirement of protecting groups on the carbohydrate. We also performed transglycosylation of an N-glycan to the N-acetylglucosaminyl peptide using endo-β-N-acetylglucosaminidase from Mucor hiemalis (Endo-M) to synthesize a glycopeptide containing a complex N-glycan.

References

Jul 2, 1998·Carbohydrate Research·K YamamotoH Kumagai
Feb 3, 2005·Bioorganic & Medicinal Chemistry Letters·Hengguang LiLai-Xi Wang
May 6, 2006·Glycobiology·Therese BuskasGeert-Jan Boons
Feb 28, 2009·Nature Reviews. Drug Discovery·Roy Jefferis
May 15, 2010·Analytical Chemistry·Martin StrohalmVladimír Havlícek
Oct 12, 2010·Carbohydrate Research·Yusuke TomabechiToshiyuki Inazu
Jul 18, 2012·The Journal of Organic Chemistry·Hironobu HojoYoshiaki Nakahara
Jan 5, 2014·Science·Martin DalzielRaymond A Dwek
Oct 30, 2016·The Journal of Biological Chemistry·Toshihiko KatohKenji Yamamoto

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Methods Mentioned

BETA
transglycosylation
glycosylation
transglycosylations

Software Mentioned

DMT
mMass

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