Advertisement

Chemo-Enzymatic Synthesis of Glycoconjugates

  • Toshiyuki Inazu

Abstract

Synthesis of glycoconjugate is one of the most important difficulties in carbohydrate chemistry. Although many chemical synthetic methods have been developed, the synthesis of glycoconjugates with natural glycan is difficult. Chemo-enzymatic syntheses of glycoconjugates using several kinds of enzymes have been reported. Sialic acid transferase has been used for the synthesis of sialo glycopeptides (Tanaka et al. 2006). Glycosylated amino acid derivative prepared using digestion of the peptide bond of glycoprotein by protease has also been applied to the synthesis of sialo glycopeptides (Yamamoto et al. 2003). In addition, the transglycosylation reaction by endo-β-N-acetylglucosaminidase (EC 3.2.1.96) has proved to be a useful method for glycoconjugate synthesis (Scheme 1).

Keywords

Sialic Acid GlcNAc Residue Transglycosylation Reaction Glycosyl Acceptor Mucor Hiemalis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Haneda K, Inazu T, Mizuno M, Iguchi R, Tanabe H, Fujimori K, Yamamoto K, Kumagai H, Tsumori K, Munekata E (2001) Chemo-enzymatic Synthesis of a Bioactive Peptide Containing a Glutamine-linked Oligosaccharide and Its Charactarization. Biochim Biophys Acta 1526:242PubMedGoogle Scholar
  2. Haneda K, Inazu T, Mizuno M, Yamamoto K (2003) Chemo-enzymatic Synthesis of Neo-glycopeptides Using Endo-M. Methods Enzymol 362(A):74PubMedCrossRefGoogle Scholar
  3. Mizuno M, Haneda K, Iguchi R, Muramoto I, Kawakami T, Aimoto S, Yamamoto K, Inazu T (1999) Synthesis of Glycopeptide Having Oligosaccharide: Chemo-enzymatic Synthesis of Eel Calcitonin Analogs Having Natural N-Linked Oligosaccharides. J Am Chem Soc 121:284CrossRefGoogle Scholar
  4. Tanaka E, Nakahara Y, Kuroda Y, Takano Y, Kojima N, Hojo H, Nakahara Y (2006) Chemoenzymic synthesis of a MUC1 glycopeptide carrying non-natural sialyl TF-β O-glycan. Biosci Biotechnol Biochem 70:2525Google Scholar
  5. Yamamoto N, Ohmori Y, Sakakibara T, Sasaki K, Juneja LR, Kajihara Y (2003) Solid-phase synthesis of sialylglycopeptides through selective esterification of the sialic acid residues of an Asn-linked complex-type sialyloligosaccharide. Angew Chem Int Ed 42:2537CrossRefGoogle Scholar

Copyright information

© Springer 2008

Authors and Affiliations

  • Toshiyuki Inazu
    • 1
  1. 1.Department of Applied Chemistry, School of Engineering, and Institute of GlycotechnologyTokai UniversityHiratsuka, KanagawaJapan

Personalised recommendations