Title:
糖オキサゾリン誘導体の製造方法
Document Type and Number:
Japanese Patent JP5301427
Kind Code:
B2
Abstract:
Disclosed is a process for producing an oxazoline derivative from a non-protected sugar in a simple manner. Also disclosed is a process for producing a glycoside by utilizing the product of the aforementioned process. A sugar oxazoline derivative is synthesized in one step in an aqueous solution from a sugar having a free hemiacetalic hydroxy group and an amido group by using a haloformamidinium derivative as a dehydrating agent. A glycoside compound is produced by using the oxazoline derivative as a sugar donor and also using a sugar dehydrogenase. The method can be applied to the production of a compound having a long sugar chain, and is therefore useful for the production of a physiologically active oligosaccharide, a carrier for a drug delivery system, a surfactant, a carbohydrate-based drug, a glycopeptide, a glycoprotein, a carbohydrate polymer or the like.
Inventors:
Shinichiro Masada
Atsushi Kobayashi
Mahito Noguchi
Tomonari Tanaka
Ashishi Eri
Atsushi Kobayashi
Mahito Noguchi
Tomonari Tanaka
Ashishi Eri
Application Number:
JP2009504035A
Publication Date:
September 25, 2013
Filing Date:
March 07, 2008
Export Citation:
Assignee:
Seikagaku Corporation
International Classes:
C07H9/06; C08B37/00; C08B37/08; A61K31/7008; A61K31/702; A61K31/7042; A61K31/7056; A61K31/715; A61P15/00; A61P15/08; A61P17/02; A61P29/00; A61P35/00; A61P35/04; A61P37/00; A61P43/00; C07H19/23
Domestic Patent References:
| JPH093088A | 1997-01-07 | |||
| JP2003012683A | 2003-01-15 | |||
| JPH093088A | 1997-01-07 | |||
| JP2003012683A | 2003-01-15 |
Foreign References:
| WO2003070960A1 | 2003-08-28 | |||
| WO2002072860A1 | 2002-09-19 |
Other References:
JPN6008021190; ＳＡＴＯＲＵ ＮＡＫＡＢＡＹＡＳＨＩ， ＣＨＲＩＳＴＯＰＨＥＲ Ｄ． ＷＡＲＲＥＮ， ａｎｄ ＲＯＧＥＲ Ｗ． ＪＥＡＮＬＯＺ: 'Ａ ｎｅｗ ｐｒｏｃｅｄｕｒｅ ｆｏｒ ｔｈｅ ｐｒｅｐａｒａｔｉｏｎ ｏｆ ｏｌｉｇｏｓａｃｃｈａｒｉｄｅ ｏｘａｚｏｌｉｎｅｓ' Ｃａｒｂｏｈｙｄｒａｔｅ Ｒｅｓｅａｒｃｈ Ｖｏｌ．１５０, 1986, Ｃ７-Ｃ１０, Ｅｌｓｅｖｉｅｒ Ｓｃｉｅｎｃｅ Ｐｕｂｌｉｓｈｅｒｓ Ｂ．Ｖ．
JPN6008021191; 'Ａ ＳＨＯＲＴ， ＳＴＥＲＥＯＳＰＥＣＩＦＩＣ ＳＹＮＴＨＥＳＩＳ ＯＦ ＤＩＨＹＤＲＯＯＸＡＺＯＬＥＳ ＦＲＯＭ ＳＥＲＩＮＥ ＡＮＤ ＴＨＲＥＯＮＩＮＥ ＤＥＲＩＶＡＴＩＶＥＳ' Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ Ｖｏｌ．３３ Ｎｏ．７, 1992, ｐ．９０７-９１０, Ｅｌｓｅｖｉｅｒ；Ｋｉｄｌｉｎｇｔｏｎ
JPN6008021195; Ｓｈｉｎ-Ｉｃｈｉｒｏ Ｓｈｏｄａ， Ｍａｓａｙａ Ｆｕｊｉｔａ， Ｃｈａｋａｐａｎ Ｌｏｈａｖｉｓａｖａｐａｎｉｃｈｉ， Ｙｏｓｈｉｎｏｒｉ Ｍｉｓａｗａ， Ｋｏｕｓｈｉｎ Ｕｓｈｉｚａｋｉ， Ｙ: 'Ｅｆｆｉｃｉｅｎｔ ｍｅｔｈｏｄ ｆｏｒ ｔｈｅ ｅｌｏｎｇａｔｉｏｎ ｏｆ ｔｈｅ Ｎ-ａｃｅｔｙｌｇｌｕｃｏｓａｍｉｎｅ ｕｎｉｔ ｂｙ ｃｏｍｂｉｎｅｄ ｕｓｅ ｏｆ ｃｈｉｔｉｎａｓｅ ａｎｄ' ＨＥＬＶＥＴＩＣＡ ＣＨＩＭＩＣＡ ＡＣＴＡ Ｖｏｌ．８５, 2002, ｐ．３９１９-３９３６, Ｖｅｒｌａｇ Ｈｅｌ
JPN6013006455; 日本化学会講演予稿集 Ｖｏｌ．８６ｔｈ Ｎｏ．２, 2006, Ｐａｇｅ．１３２５
JPN6013006456; 化学系学協会東北大会プログラムおよび講演予稿集 Ｖｏｌ．２００５, 2005, Ｐａｇｅ．２１１
JPN6013006457; 化学系学協会連合東北地方大会プログラムおよび講演予稿集 Ｖｏｌ．２００３, 2003, Ｐａｇｅ．６３
JPN6008021187; Ｊｕｎ-ｉｃｈｉ Ｋａｄｏｋａｗａ， Ｍｉｔｓｕｍａｓａ Ｍｉｔｏ， Ｓａｔｏｓｈｉ Ｔａｋａｈａｓｈｉ， Ｍａｓａｔｏ Ｎｏｇｕｃｈｉ， ａｎｄ Ｓｈｉｎ-ｉｃｈｉｒｏ Ｓｈｏｄａ: 'ＤＩＲＥＣＴ ＣＯＮＣＥＲＳＩＯＮ ＯＦ ２-ＡＣＥＴＡＭＩＤＯ-２-ＤＥＯＸＹＳＵＧＡＲＳ ＴＯ １，２-ＯＸＡＺＯＬＩＮＥ ＤＥＲＩＶＡＴＩＶＥＳ ＢＹ ＤＥＨＹＤＲＡＴＩＶＥ ＣＹＣＬＩＺＡＴＩ' ＨＥＴＥＲＯＣＹＣＬＥＳ Ｖｏｌ．６３ Ｎｏ．７, 2004, ｐ．１５３１-１５３５, 日本複素環化学研究所
JPN6008021188; 阿武喜美子・瀬野信子: 糖化学の基礎 , 1995, ｐ．１７２-１７４, 講談社
JPN6008021190; ＳＡＴＯＲＵ ＮＡＫＡＢＡＹＡＳＨＩ， ＣＨＲＩＳＴＯＰＨＥＲ Ｄ． ＷＡＲＲＥＮ， ａｎｄ ＲＯＧＥＲ Ｗ． ＪＥＡＮＬＯＺ: 'Ａ ｎｅｗ ｐｒｏｃｅｄｕｒｅ ｆｏｒ ｔｈｅ ｐｒｅｐａｒａｔｉｏｎ ｏｆ ｏｌｉｇｏｓａｃｃｈａｒｉｄｅ ｏｘａｚｏｌｉｎｅｓ' Ｃａｒｂｏｈｙｄｒａｔｅ Ｒｅｓｅａｒｃｈ Ｖｏｌ．１５０, 1986, Ｃ７-Ｃ１０, Ｅｌｓｅｖｉｅｒ Ｓｃｉｅｎｃｅ Ｐｕｂｌｉｓｈｅｒｓ Ｂ．Ｖ．
JPN6008021191; 'Ａ ＳＨＯＲＴ， ＳＴＥＲＥＯＳＰＥＣＩＦＩＣ ＳＹＮＴＨＥＳＩＳ ＯＦ ＤＩＨＹＤＲＯＯＸＡＺＯＬＥＳ ＦＲＯＭ ＳＥＲＩＮＥ ＡＮＤ ＴＨＲＥＯＮＩＮＥ ＤＥＲＩＶＡＴＩＶＥＳ' Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ Ｖｏｌ．３３ Ｎｏ．７, 1992, ｐ．９０７-９１０, Ｅｌｓｅｖｉｅｒ；Ｋｉｄｌｉｎｇｔｏｎ
JPN6008021195; Ｓｈｉｎ-Ｉｃｈｉｒｏ Ｓｈｏｄａ， Ｍａｓａｙａ Ｆｕｊｉｔａ， Ｃｈａｋａｐａｎ Ｌｏｈａｖｉｓａｖａｐａｎｉｃｈｉ， Ｙｏｓｈｉｎｏｒｉ Ｍｉｓａｗａ， Ｋｏｕｓｈｉｎ Ｕｓｈｉｚａｋｉ， Ｙ: 'Ｅｆｆｉｃｉｅｎｔ ｍｅｔｈｏｄ ｆｏｒ ｔｈｅ ｅｌｏｎｇａｔｉｏｎ ｏｆ ｔｈｅ Ｎ-ａｃｅｔｙｌｇｌｕｃｏｓａｍｉｎｅ ｕｎｉｔ ｂｙ ｃｏｍｂｉｎｅｄ ｕｓｅ ｏｆ ｃｈｉｔｉｎａｓｅ ａｎｄ' ＨＥＬＶＥＴＩＣＡ ＣＨＩＭＩＣＡ ＡＣＴＡ Ｖｏｌ．８５, 2002, ｐ．３９１９-３９３６, Ｖｅｒｌａｇ Ｈｅｌ
JPN6013006455; 日本化学会講演予稿集 Ｖｏｌ．８６ｔｈ Ｎｏ．２, 2006, Ｐａｇｅ．１３２５
JPN6013006456; 化学系学協会東北大会プログラムおよび講演予稿集 Ｖｏｌ．２００５, 2005, Ｐａｇｅ．２１１
JPN6013006457; 化学系学協会連合東北地方大会プログラムおよび講演予稿集 Ｖｏｌ．２００３, 2003, Ｐａｇｅ．６３
JPN6008021191; 'Ａ ＳＨＯＲＴ， ＳＴＥＲＥＯＳＰＥＣＩＦＩＣ ＳＹＮＴＨＥＳＩＳ ＯＦ ＤＩＨＹＤＲＯＯＸＡＺＯＬＥＳ ＦＲＯＭ ＳＥＲＩＮＥ ＡＮＤ ＴＨＲＥＯＮＩＮＥ ＤＥＲＩＶＡＴＩＶＥＳ' Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ Ｖｏｌ．３３ Ｎｏ．７, 1992, ｐ．９０７-９１０, Ｅｌｓｅｖｉｅｒ；Ｋｉｄｌｉｎｇｔｏｎ
JPN6008021195; Ｓｈｉｎ-Ｉｃｈｉｒｏ Ｓｈｏｄａ， Ｍａｓａｙａ Ｆｕｊｉｔａ， Ｃｈａｋａｐａｎ Ｌｏｈａｖｉｓａｖａｐａｎｉｃｈｉ， Ｙｏｓｈｉｎｏｒｉ Ｍｉｓａｗａ， Ｋｏｕｓｈｉｎ Ｕｓｈｉｚａｋｉ， Ｙ: 'Ｅｆｆｉｃｉｅｎｔ ｍｅｔｈｏｄ ｆｏｒ ｔｈｅ ｅｌｏｎｇａｔｉｏｎ ｏｆ ｔｈｅ Ｎ-ａｃｅｔｙｌｇｌｕｃｏｓａｍｉｎｅ ｕｎｉｔ ｂｙ ｃｏｍｂｉｎｅｄ ｕｓｅ ｏｆ ｃｈｉｔｉｎａｓｅ ａｎｄ' ＨＥＬＶＥＴＩＣＡ ＣＨＩＭＩＣＡ ＡＣＴＡ Ｖｏｌ．８５, 2002, ｐ．３９１９-３９３６, Ｖｅｒｌａｇ Ｈｅｌ
JPN6013006455; 日本化学会講演予稿集 Ｖｏｌ．８６ｔｈ Ｎｏ．２, 2006, Ｐａｇｅ．１３２５
JPN6013006456; 化学系学協会東北大会プログラムおよび講演予稿集 Ｖｏｌ．２００５, 2005, Ｐａｇｅ．２１１
JPN6013006457; 化学系学協会連合東北地方大会プログラムおよび講演予稿集 Ｖｏｌ．２００３, 2003, Ｐａｇｅ．６３
JPN6008021187; Ｊｕｎ-ｉｃｈｉ Ｋａｄｏｋａｗａ， Ｍｉｔｓｕｍａｓａ Ｍｉｔｏ， Ｓａｔｏｓｈｉ Ｔａｋａｈａｓｈｉ， Ｍａｓａｔｏ Ｎｏｇｕｃｈｉ， ａｎｄ Ｓｈｉｎ-ｉｃｈｉｒｏ Ｓｈｏｄａ: 'ＤＩＲＥＣＴ ＣＯＮＣＥＲＳＩＯＮ ＯＦ ２-ＡＣＥＴＡＭＩＤＯ-２-ＤＥＯＸＹＳＵＧＡＲＳ ＴＯ １，２-ＯＸＡＺＯＬＩＮＥ ＤＥＲＩＶＡＴＩＶＥＳ ＢＹ ＤＥＨＹＤＲＡＴＩＶＥ ＣＹＣＬＩＺＡＴＩ' ＨＥＴＥＲＯＣＹＣＬＥＳ Ｖｏｌ．６３ Ｎｏ．７, 2004, ｐ．１５３１-１５３５, 日本複素環化学研究所
JPN6008021188; 阿武喜美子・瀬野信子: 糖化学の基礎 , 1995, ｐ．１７２-１７４, 講談社
JPN6008021190; ＳＡＴＯＲＵ ＮＡＫＡＢＡＹＡＳＨＩ， ＣＨＲＩＳＴＯＰＨＥＲ Ｄ． ＷＡＲＲＥＮ， ａｎｄ ＲＯＧＥＲ Ｗ． ＪＥＡＮＬＯＺ: 'Ａ ｎｅｗ ｐｒｏｃｅｄｕｒｅ ｆｏｒ ｔｈｅ ｐｒｅｐａｒａｔｉｏｎ ｏｆ ｏｌｉｇｏｓａｃｃｈａｒｉｄｅ ｏｘａｚｏｌｉｎｅｓ' Ｃａｒｂｏｈｙｄｒａｔｅ Ｒｅｓｅａｒｃｈ Ｖｏｌ．１５０, 1986, Ｃ７-Ｃ１０, Ｅｌｓｅｖｉｅｒ Ｓｃｉｅｎｃｅ Ｐｕｂｌｉｓｈｅｒｓ Ｂ．Ｖ．
JPN6008021191; 'Ａ ＳＨＯＲＴ， ＳＴＥＲＥＯＳＰＥＣＩＦＩＣ ＳＹＮＴＨＥＳＩＳ ＯＦ ＤＩＨＹＤＲＯＯＸＡＺＯＬＥＳ ＦＲＯＭ ＳＥＲＩＮＥ ＡＮＤ ＴＨＲＥＯＮＩＮＥ ＤＥＲＩＶＡＴＩＶＥＳ' Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ Ｖｏｌ．３３ Ｎｏ．７, 1992, ｐ．９０７-９１０, Ｅｌｓｅｖｉｅｒ；Ｋｉｄｌｉｎｇｔｏｎ
JPN6008021195; Ｓｈｉｎ-Ｉｃｈｉｒｏ Ｓｈｏｄａ， Ｍａｓａｙａ Ｆｕｊｉｔａ， Ｃｈａｋａｐａｎ Ｌｏｈａｖｉｓａｖａｐａｎｉｃｈｉ， Ｙｏｓｈｉｎｏｒｉ Ｍｉｓａｗａ， Ｋｏｕｓｈｉｎ Ｕｓｈｉｚａｋｉ， Ｙ: 'Ｅｆｆｉｃｉｅｎｔ ｍｅｔｈｏｄ ｆｏｒ ｔｈｅ ｅｌｏｎｇａｔｉｏｎ ｏｆ ｔｈｅ Ｎ-ａｃｅｔｙｌｇｌｕｃｏｓａｍｉｎｅ ｕｎｉｔ ｂｙ ｃｏｍｂｉｎｅｄ ｕｓｅ ｏｆ ｃｈｉｔｉｎａｓｅ ａｎｄ' ＨＥＬＶＥＴＩＣＡ ＣＨＩＭＩＣＡ ＡＣＴＡ Ｖｏｌ．８５, 2002, ｐ．３９１９-３９３６, Ｖｅｒｌａｇ Ｈｅｌ
JPN6013006455; 日本化学会講演予稿集 Ｖｏｌ．８６ｔｈ Ｎｏ．２, 2006, Ｐａｇｅ．１３２５
JPN6013006456; 化学系学協会東北大会プログラムおよび講演予稿集 Ｖｏｌ．２００５, 2005, Ｐａｇｅ．２１１
JPN6013006457; 化学系学協会連合東北地方大会プログラムおよび講演予稿集 Ｖｏｌ．２００３, 2003, Ｐａｇｅ．６３
Attorney, Agent or Firm:
Kazuo Shigenobu
Mizuno Akinori
Hideo Shimizu
Yuichi Takagi
Yoshinao Nakano
Ryoichi Mizobuchi
Hideki Akiba
Mizuno Akinori
Hideo Shimizu
Yuichi Takagi
Yoshinao Nakano
Ryoichi Mizobuchi
Hideki Akiba