Synthesis of a Trisaccharide Repeating Unit of the O‐Antigen from Burkholderia multivorans and Its Oligomers. Issue 32 (12th October 2015)

• Record Type: Journal Article
• Authors: Zhang, Xin; Gu, Guofeng; Guo, Zhongwu
• Is Part Of: European journal of organic chemistry. Issue 32(2015)
• Page Start: 7075
• Page End: 7085
• Publication Date: 2015-10-12
• Subjects: Synthesis design -- Total synthesis -- Diastereoselectivity -- Carbohydrates -- Glycosylation -- Medicinal chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500964
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Burkholderia multivorans is a Gram‐negative bacterium, and an important opportunistic human pathogen that can cause fatal infections. Its O‐antigens are useful templates for the development of carbohydrate‐based vaccines. A highly convergent and efficient strategy was developed for the synthesis of tri‐, hexa‐, and nonasaccharide fragments of the O‐antigen of B. multivorans species Y. In these syntheses, a trisaccharyl thioglycoside, which was assembled from thiomannoside acceptor and rhamnosyl and mannosyl trichloroacetimidate donors, was used as a key building block. Glycosylation of 3‐azidopropanol with the trisaccharyl donor followed by global deprotection gave the target trisaccharide. The trisaccharyl donor was also used to elongate the carbohydrate chain to obtain the dimer and trimer in a [3 + 3] and [3 + 3 + 3] manner. All of the synthetic targets have a free amino group at their reducing end to facilitate further derivatization, such as conjugation with other functional biomolecules. Abstract : Tri‐, hexa‐, and nonasaccharide derivatives related to the O‐antigen of B. multivorans (species Y) were synthesized for the first time using a highly convergent and efficient strategy.