Efficient synthesis of a 6-deoxytalose tetrasaccharide related to the antigenic O-polysaccharide produced by Aggregatibacter actinomycetemcomitans serotype c.
Concise synthesis of a 6-deoxy-alpha-L-talose tetrasaccharide, 6-deoxy-alpha-L-Talp-(1-->3)-6-deoxy-alpha-L-Talp-(1-->2)-6-deoxy-alpha-L-Talp-(1-->3)-6-deoxy-alpha-L-Talp, the dimer of the disaccharide repeating unit of the OPS from Aggregatibacter actinomycetemcomitans serotype c, has been accomplished through suitable protecting group manipulations and stereoselective glycosylation starting from commercially available L-rhamnose. The target oligosaccharide in the form of its p-methoxyphenyl glycoside is suitable for further glycoconjugate formation via selective cleavage of this group.
Cai
Xiangyan
X
Key Lab of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing, China.
Zong
Guanghui
G
Xu
Yanjun
Y
Zhang
Jianjun
J
Liang
Xiaomei
X
Wang
Daoquan
D
D002240:Carbohydrate Sequence; D003837:Deoxy Sugars / Q000737:chemistry*; D006031:Glycosylation; D006601:Hexoses / Q000737:chemistry*; D008969:Molecular Sequence Data; D019081:O Antigens / Q000096:biosynthesis* / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D015661:Pasteurellaceae / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
D003837:Deoxy Sugars; D006601:Hexoses; D019081:O Antigens; D009844:Oligosaccharides; C011754:6-deoxytalose