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Sugar Amino Acid
No.125(March 2007)
The sugar amino acid 1 is a glycoamino acid in which N-acetyl-D-glucosamine is linked to the asparagine by an N-glycosidic linkage, and can be used for the synthesis of asparagine linked glycoproteins or glycopeptides. For instance, when 1 is reacted with a peptide supported on silica gel, followed by transglycosylation with galactose or sialic acid using glycosyltransferase, its oligosaccharides can be elongated.2) Moreover, this glycoamino acid is also used for the “Chemo-Enzymatic Method”, by which the complex glycopeptide 4 is synthesized by ransglycosylation of an oligosaccharide of the natural N-linked glycopeptide 3 to an N-acetyl-D-glucosamine moiety of the glycopeptide 2, using Endo-M.3)
References
- 1)Preparation of asparagine-containing glycopeptides
- 2)Synthesis of glycopeptides and oligosaccharides
- 3)Chemo-enzymatic synthesis of bioactive complex glycopeptides
- a)M. Mizuno, K. Haneda, R. Iguchi, I. Muramoto, T. Kawakami, S. Aimoto. K. Yamamoto, T. Inazu, J. Am. Chem. Soc., 1999, 121, 284.
- b)K. Haneda, T. Inazu, K. Yamamoto, Bioscience & Industry 2002, 60, 159.
- a)M. Mizuno, K. Haneda, R. Iguchi, I. Muramoto, T. Kawakami, S. Aimoto. K. Yamamoto, T. Inazu, J. Am. Chem. Soc., 1999, 121, 284.
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