Oligosaccharide, method for producing it and pharmaceutical composition containing it
申请人:Seikagaku Corporation
公开号:EP1018515A1
公开(公告)日:2000-07-12
A method for producing oligosaccharides, including those usable as anti-inflammatory agent or anti-allergy agent, represented by the following general formula (3):
wherein R10 and R11 each independently represent a hydrogen atom or -SO3M where M represents a proton or a monovalent cation, Ac represents an acetyl group, R12 represents a hydrogen atom or an anomeric substituent (a 6-O-sulfated N-acetylglucosamine residue, an alkyl group, a glycerol residue, an O-alkylglycerol residue, a cholesterol residue, a cholestanyl group, a ceramide residue, a phospholipid residue, a biotin residue, or a peptide residue), and Z represents an oxygen atom or -NHCO-,
which method comprises at least a step of carrying out glycosidic linkage formation between a monosaccharide represented by the following general formula (1):
wherein R1 and R2 each independently represent an aralkyl group, R3 represents an acyl group or a silyl group, R4 represents a protective group for an amino group, and R5 represents a leaving group, and
a monosaccharide represented by the following general formula (2):
wherein R6 and R8 each independently represent an aralkyl group, R7 represents an acyl group or a silyl group, R9 represents an aralkyl group or the anomeric substituent, and Z is as defined above.
一种生产由以下通式(3)代表的低聚糖,包括可用作抗炎剂或抗过敏剂的低聚糖的方法:
其中 R10 和 R11 各自独立地代表氢原子或-SO3M,其中 M 代表质子或一价阳离子,Ac 代表乙酰基,R12 代表氢原子或异构取代基(6-O-硫酸化的 N-乙酰氨基葡萄糖残基、烷基、甘油残基、O-烷基甘油残基、胆固醇残基、胆甾烷基、神经酰胺残基、磷脂残基、生物素残基或肽残基),Z 代表氧原子或-NHCO-、
该方法至少包括以下通式(1)所代表的单糖之间形成糖苷键的步骤:
其中 R1 和 R2 各自独立地代表芳烷基,R3 代表酰基或硅烷基,R4 代表氨基的保护基,R5 代表离去基团,以及
由以下通式(2)代表的单糖:
其中 R6 和 R8 各自独立地代表一个芳烷基,R7 代表一个酰基或硅烷基,R9 代表一个芳烷基或异构取代基,Z 如上所定义。