Title:
PROCESS FOR PRODUCING NOVEL SIALO-SUGAR CHAIN
Document Type and Number:
WIPO Patent Application WO/2013/042581
Kind Code:
A1
Abstract:
Provided are: a novel sialo-sugar chain; a process for producing said sialo-sugar chain; and production equipment for said sialo -sugar chain. The novel sialo-sugar chain can be easily and efficiently mass-produced by reacting a sugar wherein one of the hydroxyl groups is substituted with an alkynyl group (hereinafter, said sugar being often referred to as "an alkynylated sugar") with a specific sialic acid donor in the presence of a sialic acid-introducing enzyme.
Inventors:
YAMAGUCHI MASANORI (JP)
Application Number:
PCT/JP2012/073181
Publication Date:
March 28, 2013
Filing Date:
September 11, 2012
Export Citation:
Assignee:
WAKAYAMA UNIVERSITY (JP)
YAMAGUCHI MASANORI (JP)
YAMAGUCHI MASANORI (JP)
International Classes:
C07H15/04; C07H15/26; C12M1/40; C12P19/26
Foreign References:
| JP2008534665A | 2008-08-28 | |||
| JPH03262495A | 1991-11-22 |
Other References:
SANDER I. VAN KASTEREN ET AL.: "Expanding the diversity of chemical protein modification allows post- translational mimicry", NATURE, vol. 446, no. 7139, 2007, pages 1105 - 1109, XP055086777
S. BAY ET AL.: "Induction of a Melanoma- Specific Antibody Response by a Monovalent, but not a Divalent, Synthetic GM2 Neoglycopeptide", CHEMMEDCHEM, vol. 4, no. 4, 2009, pages 582 - 587, XP055108442
SEBASTIEN FORT ET AL.: "Biosynthesis of conjugatable saccharidic moieties of GM2 and GM3 gangliosides by engineered E. coli", CHEMICAL COMMUNICATIONS, no. 20, 2005, pages 2558 - 2560, XP055147366
ALIAKSEI V. PUKIN ET AL.: "GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900 MHz NMR analysis", CARBOHYDRATE RESEARCH, vol. 343, no. 4, 2008, pages 636 - 650, XP022497588
HONGZHI CAO ET AL.: "Parallel chemoenzymatic synthesis of sialosides containing a C5-diversified sialic acid", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 20, 2009, pages 5869 - 5871, XP026640589
KATSUMI AJISAKA ET AL.: "Regioselective transglycosylation in the synthesis of oligosaccharides: comparison of beta-galactosidases and sialidases of various origins", CARBOHYDRATE RESEARCH, vol. 259, no. 1, 1994, pages 103 - 115, XP002961424
DIRK SCHMIDT ET AL.: "Chemoenzymatic Synthesis of Sialyl Oligosaccharides with Sialidases Employing Transglycosylation Methodology", JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 25, 2000, pages 8518 - 8526, XP055147369
JOACHIM THIEM ET AL.: "Chemoenzymatische Synthesen von Sialyl- Oligosacchariden mit immobilisierter Sialidase", ANGEWANDTE CHEMIE, vol. 103, no. 11, 1991, pages 1521 - 1523, XP055155091
BIOSCI. BIOTECH. BIOCHEM., vol. 56, no. 10, 1992, pages 1557 - 1561
VOLKER ESCHENFELDER ET AL., CABOHYDR. RES., vol. 162, 1987, pages 294 - 297
K.B. SHARPLESS ET AL., ANGEW. CHEM. INT. ED., vol. 41, 2002, pages 2596 - 2599
M. YAMAGUCHI ET AL., TETRAHEDRON LETT., vol. 47, 2006, pages 7455 - 7458
See also references of EP 2759548A4
S. BAY ET AL.: "Induction of a Melanoma- Specific Antibody Response by a Monovalent, but not a Divalent, Synthetic GM2 Neoglycopeptide", CHEMMEDCHEM, vol. 4, no. 4, 2009, pages 582 - 587, XP055108442
SEBASTIEN FORT ET AL.: "Biosynthesis of conjugatable saccharidic moieties of GM2 and GM3 gangliosides by engineered E. coli", CHEMICAL COMMUNICATIONS, no. 20, 2005, pages 2558 - 2560, XP055147366
ALIAKSEI V. PUKIN ET AL.: "GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900 MHz NMR analysis", CARBOHYDRATE RESEARCH, vol. 343, no. 4, 2008, pages 636 - 650, XP022497588
HONGZHI CAO ET AL.: "Parallel chemoenzymatic synthesis of sialosides containing a C5-diversified sialic acid", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 20, 2009, pages 5869 - 5871, XP026640589
KATSUMI AJISAKA ET AL.: "Regioselective transglycosylation in the synthesis of oligosaccharides: comparison of beta-galactosidases and sialidases of various origins", CARBOHYDRATE RESEARCH, vol. 259, no. 1, 1994, pages 103 - 115, XP002961424
DIRK SCHMIDT ET AL.: "Chemoenzymatic Synthesis of Sialyl Oligosaccharides with Sialidases Employing Transglycosylation Methodology", JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 25, 2000, pages 8518 - 8526, XP055147369
JOACHIM THIEM ET AL.: "Chemoenzymatische Synthesen von Sialyl- Oligosacchariden mit immobilisierter Sialidase", ANGEWANDTE CHEMIE, vol. 103, no. 11, 1991, pages 1521 - 1523, XP055155091
BIOSCI. BIOTECH. BIOCHEM., vol. 56, no. 10, 1992, pages 1557 - 1561
VOLKER ESCHENFELDER ET AL., CABOHYDR. RES., vol. 162, 1987, pages 294 - 297
K.B. SHARPLESS ET AL., ANGEW. CHEM. INT. ED., vol. 41, 2002, pages 2596 - 2599
M. YAMAGUCHI ET AL., TETRAHEDRON LETT., vol. 47, 2006, pages 7455 - 7458
See also references of EP 2759548A4
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
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