Title:
SUGAR CHAIN CONTAINING 4-POSITION HALOGENATED GALACTOSE AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2006/088017
Kind Code:
A1
Abstract:
An oligosaccharide having at an end thereof a 4-position halogenated galactose residue represented by the following formula (I); a transferase inhibitor containing the oligosaccharide; a method of inhibiting a sugar chain elongation reaction by glycosyltransferase with the use of the inhibitor; etc. Further, there is provided a process for producing a 4-position halogenated galactose sugar nucleotide represented by the formula (II) with the use of microbe-derived galactokinase and microbe-derived hexose-1-phosphate uridyl transferase. (I) (wherein X is a halogen atom; and R is a monosaccharide, an oligosaccharide or a carrier) (II) (wherein each of R1 to R3 is hydroxyl, acetyl, a halogen atom or a hydrogen atom; X is a halogen atom; and M is a hydrogen ion or a metal ion). Thus, there are provided a sugar chain containing 4-position halogenated galactose whose use in pharmaceutical products, etc. is promising, and applications thereof.
Inventors:
NISHIMURA SHIN-ICHIRO (JP)
NAGAHORI NORIKO (JP)
HAMAMOTO TOMOKI (JP)
OKUYAMA KIYOSHI (JP)
NOGUCHI TOSHITADA (JP)
NAGAHORI NORIKO (JP)
HAMAMOTO TOMOKI (JP)
OKUYAMA KIYOSHI (JP)
NOGUCHI TOSHITADA (JP)
Application Number:
PCT/JP2006/302529
Publication Date:
August 24, 2006
Filing Date:
February 14, 2006
Export Citation:
Assignee:
UNIV HOKKAIDO NAT UNIV CORP (JP)
YAMASA CORP (JP)
NISHIMURA SHIN-ICHIRO (JP)
NAGAHORI NORIKO (JP)
HAMAMOTO TOMOKI (JP)
OKUYAMA KIYOSHI (JP)
NOGUCHI TOSHITADA (JP)
YAMASA CORP (JP)
NISHIMURA SHIN-ICHIRO (JP)
NAGAHORI NORIKO (JP)
HAMAMOTO TOMOKI (JP)
OKUYAMA KIYOSHI (JP)
NOGUCHI TOSHITADA (JP)
International Classes:
C12P19/32; A61K31/7028; A61P35/00; A61P43/00; C07H15/08
Foreign References:
| JP2004041118A | 2004-02-12 | |||
| JP2001511812A | 2001-08-14 | |||
| JPH0787927A | 1995-04-04 | |||
| JPH02501440A | 1990-05-24 | |||
| JPS5835196A | 1983-03-01 | |||
| JPS5829795A | 1983-02-22 | |||
| JPS57102898A | 1982-06-26 | |||
| JPS5287275A | 1977-07-20 |
Other References:
SOFIAN A.M. AND LEE C.K.: "Synthesis and taste properties of 4,1',4',6'-tetrahalodeoxysucrose analogues", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 22, no. 3 & 4, 2003, pages 185 - 206, XP008063993
LEE C.K., KANG H.C., LINDEN A.: "Synthesis, structure, and sweetness of 4-chloro-4-deoxy-alpha-D-galactopyranosyl, 4,6-trichloro-1,4,6-trideoxy-beta-D-tagatofuranoside", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 18, no. 2, 1999, pages 241 - 253, XP008063991
SUAMI T. ET AL.: "Molecular mechanisms of sweet taste. V. Sucralose and its derivatives", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 13, no. 8, 1994, pages 1079 - 1092, XP008063992
GARCIA R.C. ET AL.: "Syntheses of hepta-, hexa-, and pentapivalates of trehalose by selective pivaloylation", CARBOHYDRATE RESEARCH, vol. 200, 25 April 1990 (1990-04-25), pages 307 - 317, XP002997967
KIHLBERG J. ET AL.: "Preparation and calculated conformations of the 2'-, 3'-, 4'-, and 6'-deoxy, 3'-O-methyl, 4'-epi, and 4'- and 6'-deoxyfluoro derivatives of methyl 4-O-alpha-D-alpha-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside)", CARBOHYDRATE RESEARCH, vol. 185, no. 2, 1 February 1989 (1989-02-01), pages 171 - 190, XP009009830
FAIRCLOUGH P.H., HOUGH L., RICHARDSON A.C.: "Derivatives of beta-D-fructofuranosyl alpha-D-galactopyranoside", CARBOHYDRATE RESEARCH, vol. 40, no. 2, 1975, pages 285 - 298, XP000571304
HOUGH L., PALMER A.K., RICHARDSON A.C.: "Chemical modification of trehalose. XIII. Synthesis of 4,4'-difluoro and 4,4'6,6'-tetrafluoro analogs", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTINS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY (1972-1999), no. 8, 1973, pages 784 - 788, XP008063989
ARITA H. AND MATSUSHIMA Y.: "Studies on the Substrate specificity of taka-amylase A. IX. Effect on the enzymic action of the terminal C-4 of phenyl alpha-maltoside", JOURNAL OF BIOCHEMISTRY, vol. 70, no. 5, November 1971 (1971-11-01), TOKYO, JAPAN, pages 795 - 801, XP008063990
LEE C.K., KANG H.C., LINDEN A.: "Synthesis, structure, and sweetness of 4-chloro-4-deoxy-alpha-D-galactopyranosyl, 4,6-trichloro-1,4,6-trideoxy-beta-D-tagatofuranoside", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 18, no. 2, 1999, pages 241 - 253, XP008063991
SUAMI T. ET AL.: "Molecular mechanisms of sweet taste. V. Sucralose and its derivatives", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 13, no. 8, 1994, pages 1079 - 1092, XP008063992
GARCIA R.C. ET AL.: "Syntheses of hepta-, hexa-, and pentapivalates of trehalose by selective pivaloylation", CARBOHYDRATE RESEARCH, vol. 200, 25 April 1990 (1990-04-25), pages 307 - 317, XP002997967
KIHLBERG J. ET AL.: "Preparation and calculated conformations of the 2'-, 3'-, 4'-, and 6'-deoxy, 3'-O-methyl, 4'-epi, and 4'- and 6'-deoxyfluoro derivatives of methyl 4-O-alpha-D-alpha-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside)", CARBOHYDRATE RESEARCH, vol. 185, no. 2, 1 February 1989 (1989-02-01), pages 171 - 190, XP009009830
FAIRCLOUGH P.H., HOUGH L., RICHARDSON A.C.: "Derivatives of beta-D-fructofuranosyl alpha-D-galactopyranoside", CARBOHYDRATE RESEARCH, vol. 40, no. 2, 1975, pages 285 - 298, XP000571304
HOUGH L., PALMER A.K., RICHARDSON A.C.: "Chemical modification of trehalose. XIII. Synthesis of 4,4'-difluoro and 4,4'6,6'-tetrafluoro analogs", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTINS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY (1972-1999), no. 8, 1973, pages 784 - 788, XP008063989
ARITA H. AND MATSUSHIMA Y.: "Studies on the Substrate specificity of taka-amylase A. IX. Effect on the enzymic action of the terminal C-4 of phenyl alpha-maltoside", JOURNAL OF BIOCHEMISTRY, vol. 70, no. 5, November 1971 (1971-11-01), TOKYO, JAPAN, pages 795 - 801, XP008063990
Attorney, Agent or Firm:
The, Patent Corporate Body Aruga Patent Office (3-6 Nihonbashiningyocho 1-chome, Chuo-k, Tokyo 13, JP)
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