Title:
RATIONAL DESIGN AND SYNTHESIS OF FUNCTIONAL GLYCOPEPTIDE
Document Type and Number:
WIPO Patent Application WO/2004/101619
Kind Code:
A1
Abstract:
A glycopeptide comprising a peptide with configuration capable of exhibiting biological activity, having glutamine at at least one amino acid residue, wherein the glutamine is modified with a sugar chain. Further, there is provided a method of preparing a functional glycopeptide, comprising the steps of (A) providing a desired peptide having glutamine at at least one amino acid residue and (B) introducing a sugar chain into the glutamine. As a result, the biological activity thereof can be significantly fortified or regulated.
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Inventors:
NISHIMURA SHINICHIRO (JP)
SATO MASAAKI (JP)
FURUIKE TETSUYA (JP)
SATO MASAAKI (JP)
FURUIKE TETSUYA (JP)
Application Number:
PCT/JP2004/006927
Publication Date:
November 25, 2004
Filing Date:
May 14, 2004
Export Citation:
Assignee:
SHIONOGI & CO (JP)
NISHIMURA SHINICHIRO (JP)
SATO MASAAKI (JP)
FURUIKE TETSUYA (JP)
NISHIMURA SHINICHIRO (JP)
SATO MASAAKI (JP)
FURUIKE TETSUYA (JP)
International Classes:
A01N37/44; A01N43/16; A23L1/305; A61K8/64; A61P3/00; A61P3/10; A61Q19/00; C12P21/00; A61K38/00; (IPC1-7): C07K14/74; A01N63/00; A23L1/305; A61K7/00; A61K38/02; A61K38/16; A61P3/00; A61P3/10; C07K14/475; C07K14/52; C07K14/575; C07K14/65; C07K14/705; C07K14/765; C07K16/00; C12N9/00; C12N15/00; C12P21/02
Other References:
NISHIMURA S. ET AL.: "Efficient method for precise preparation of glycopeptides an glycoprotein", POLYMER PREPRINTS, vol. 48, no. 3, 1999, pages 481, XP002987011
YAN S.-C.B. ET AL.: "Neoglycoproteins: In vitro introduction of glycosyl units at glutamines in beta-casein using transglutaminase", BIOCHEMISTRY, vol. 23, no. 16, 1984, pages 3759 - 3765, XP002027518
RAMOS D. ET AL.: "Chemoenzymatic synthesis of neoglycopeptides: application to an alpha-Gal-terminated neoglycopeptide", J. ORG. CHEM., vol. 66, no. 9, 2001, pages 2948 - 2956, XP002981410
YAMAMOTO K.: "Chemo-enzymatic synthesis of bioactive glycopeptide using microbial endoglycosidase", JOURNAL OF BIOSCIENCE AND BIOENGINEERING, vol. 92, no. 6, 2001, pages 493 - 501, XP002981411
HANEDA K. ET AL.: "Chemo-enzymatic synthesis of a bioactive peptide containing a glutamine-linked oligosaccharide and its characterization", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1526, no. 3, 2001, pages 242 - 248, XP004245551
YOUNG R.J. ET AL.: "Secretion of recombinant human IgE-Fc by mammalian cells and biological activity of glycosylation site mutants", PROTEIN ENGINEERING, vol. 8, no. 2, 1995, pages 193 - 199, XP000500391
SATO M. ET AL.: "Site-specific introduction of sialic acid into insulin", ANGEW. CHEM. INT. ED., vol. 43, no. 12, 12 March 2004 (2004-03-12), pages 1516 - 1520, XP002981412
YAN S.-C.B. ET AL.: "Neoglycoproteins: In vitro introduction of glycosyl units at glutamines in beta-casein using transglutaminase", BIOCHEMISTRY, vol. 23, no. 16, 1984, pages 3759 - 3765, XP002027518
RAMOS D. ET AL.: "Chemoenzymatic synthesis of neoglycopeptides: application to an alpha-Gal-terminated neoglycopeptide", J. ORG. CHEM., vol. 66, no. 9, 2001, pages 2948 - 2956, XP002981410
YAMAMOTO K.: "Chemo-enzymatic synthesis of bioactive glycopeptide using microbial endoglycosidase", JOURNAL OF BIOSCIENCE AND BIOENGINEERING, vol. 92, no. 6, 2001, pages 493 - 501, XP002981411
HANEDA K. ET AL.: "Chemo-enzymatic synthesis of a bioactive peptide containing a glutamine-linked oligosaccharide and its characterization", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1526, no. 3, 2001, pages 242 - 248, XP004245551
YOUNG R.J. ET AL.: "Secretion of recombinant human IgE-Fc by mammalian cells and biological activity of glycosylation site mutants", PROTEIN ENGINEERING, vol. 8, no. 2, 1995, pages 193 - 199, XP000500391
SATO M. ET AL.: "Site-specific introduction of sialic acid into insulin", ANGEW. CHEM. INT. ED., vol. 43, no. 12, 12 March 2004 (2004-03-12), pages 1516 - 1520, XP002981412
Attorney, Agent or Firm:
Yamamoto, Shusaku (Crystal Tower 2-27, Shiromi 1-chome, Chuo-k, Osaka-shi Osaka 15, JP)
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