No.125
Sugar Amino Acid
| A1614 | Nω-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-Nα-(tert-butoxycarbonyl)-L-asparagine |
100mg |
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
K. Haneda, T. Inazu, K. Yamamoto, H. Kumagai, Y. Nakahara, A. Kobata, Carbohydr. Res., 1996, 292, 61.
2) Synthesis of glycopeptides and oligosaccharides
M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc., 1994, 116, 1135.
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.
K. Haneda, T. Inazu, K. Yamamoto, H. Kumagai, Y. Nakahara, A. Kobata, Carbohydr. Res., 1996, 292, 61.
2) Synthesis of glycopeptides and oligosaccharides
M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc., 1994, 116, 1135.
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.
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