Process for producing sugar chain asparagine derivative

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process...

Reexamination Certificate

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C435S068100, C435S085000, C435S091530, C435S101000, C536S001110, C536S017200, C536S127000

Reexamination Certificate

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07955819

ABSTRACT:
A process for preparing asparagine-linked oligosaccharide derivatives including the steps of: (a) treating a delipidated egg yolk with a protease to obtain a mixture of peptide-linked oligosaccharides, (b) treating the mixture of peptide-linked oligosaccharides with a peptidase to obtain a mixture of asparagine-linked oligosaccharides, (c) introducing a lipophilic protective group into the asparagine-linked oligosaccharides in the mixture to obtain a mixture of asparagine-linked oligosaccharide derivatives, and (d) subjecting the mixture of asparagine-linked oligosaccharide derivatives to chromatography to separate the mixture into individual asparagine-linked oligosaccharide derivatives.

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patent: 2004/0181054 (2004-09-01), Kajihara et al.
patent: 08099988 (1996-04-01), None
patent: 03/008431 (2003-01-01), None
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Inazu Toshiyuki et al., “Preparation of Fmoc-asparagine Derivatives Having NaturalN-linked Oligosaccharide, and its Application to the Synthesis of Glycopeptides”,Peptide Science, 1999, vol. 1998, pp. 153-156.
Inazu, Toshiyuki, et. al., “Preparation of Fmoc-asparagine Derivatives Having Natural N-Linked Oligosaccharide, and Its Application to the Synthesis of Glycopeptides”; Peptide Science 1998: M. Kondo (Ed.), Protein Research Foundation, Osaka (1999); pp. 153-156.
Koketsu, Mamoru, et. al., “Sialyloligosaccharides of Delipidated Egg Yolk Fraction”; Journal of Food Science, vol. 58, No. 4 (1993); pp. 743-747.
Yamamoto, Kenji; “Chemo-Enzymatic Synthesis of Bioactive Glycopeptide Using Microbial Endoglycosidase”; Journal of Bioscience and Bioengineering, vol. 92, No. 6 (2001); pp. 493-501.
Seko, Akira. et al., “Occurrence of a sialylglycopeptide and free sialylglycans in hen's egg yolk”,Biochemica et Biophysica Acta, vol. 1335, (1997) pp. 23-32.
Lin, Chun-Hung, et al., “Enzymatic Synthesis of a Sialyl Lewis X Dimer from Egg Yolk as an Inhibitor of E-Selectin”; Biorganic & Medicinal Chemistry, vol. 3, No. 12 (1995); pp. 1625-1630.

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