755002-56-3Relevant academic research and scientific papers
A convergent synthesis of 6-o-branched β-Glucan oligosaccharides
Liao, Guochao,Burgula, Srinivas,Zhou, Zhifang,Guo, Zhongwu
, p. 2942 - 2951 (2015)
β-Glucans are important carbohydrate antigens that are found on the surface of fungal cells, and they could be useful for the development of antifungal vaccines. This paper describes a highly convergent and efficient strategy for the synthesis of structur
Convergent Synthesis of Branched β-Glucan Tridecasaccharides Ready for Conjugation
Zhou, Xin,Long, Qing,Li, Dongwei,Gao, Jingru,Sun, Qikai,Sun, Shaozi,Su, Yong,Wang, Peng,Peng, Wenjie,Li, Ming
, p. 2435 - 2448 (2021/04/21)
Structurally defined and pure oligosaccharides corresponding to β-glucans have attracted great attention because of their potential properties as immunostimulating agents and as antigens of vaccine candidates. We herein describe a convergent synthesis of ready-to-conjugate tridecasaccharides composed of a β-1,3-glucan nonasaccharide backbone and a β-1,6-glucan tetrasaccharide branch. The assembly was achieved by employing trichloroacetimidate glycosylations and features the gram-scale preparation of the nonasaccharide backbone and installation of the tetrasaccharide branch involving orthoester rearrangement to the glycoside.
Synthesis and Immunological Studies of Oligosaccharides that Consist of the Repeating Unit of Streptococcus pneumoniae Serotype 3 Capsular Polysaccharide
Xiong, Chenghe,Feng, Shaojie,Qiao, Yin,Guo, Zhongwu,Gu, Guofeng
, p. 8205 - 8216 (2018/05/29)
A highly convergent and efficient strategy was developed for the chemical synthesis of complex oligosaccharides of Streptococcus pneumoniae type 3 capsular polysaccharides that contain multiple glucuronic acid units. Once the oligoglucosides were efficiently and stereoselectively assembled, the designated glucose units were regioselectively oxidized to glucuronic acid in one step at the final synthetic stage, which helped avoid difficult glycosylations that involved glucuronic acid. The target oligosaccharides had a free amino group at the reducing terminus and varied caps at the non-reducing terminus to enable further modification and structure–activity relationship studies. Immunological evaluations of the oligosaccharide–tetanus toxoid conjugates showed that they elicited robust T-cell-dependent immunoglobulin G antibody responses and that the sugar chain length had a major impact on their immunological properties. In particular, the penta- and hexasaccharides were identified as promising antigens for vaccine development.
Oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, preparation method and applications thereof
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, (2017/10/13)
The present invention relates to an oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, a preparation method and applications thereof, wherein the structure general formula of the oligosaccharide conjugate is define
Synthesis and Immunological Studies of Linear Oligosaccharides of β-Glucan As Antigens for Antifungal Vaccine Development
Liao, Guochao,Zhou, Zhifang,Burgula, Srinivas,Liao, Jun,Yuan, Cheng,Wu, Qiuye,Guo, Zhongwu
, p. 466 - 476 (2015/03/30)
Antifungal vaccines have recently engendered considerable excitement for counteracting the resurgence of fungal infections. In this context, β-glucan, which is abundantly expressed on all fungal cell surfaces, functionally necessary for fungi, and immunologically active, is an attractive target antigen. Aiming at the development of effective antifungal vaccines based on β-glucan, a series of its oligosaccharide derivatives was designed, synthesized, and coupled with a carrier protein, keyhole limpet hemocyanin (KLH), to form new semisynthetic glycoconjugate vaccines. In this article, a convergent and effective synthetic strategy using preactivation-based iterative glycosylation was developed for the designed oligosaccharides. The strategy can be widely useful for rapid construction of large oligo-β-glucans with shorter oligosaccharides as building blocks. The KLH conjugates of the synthesized β-glucan hexa-, octa-, deca-, and dodecasaccharides were demonstrated to elicit high titers of antigen-specific total and IgG antibodies in mice, suggesting the induction of functional T cell-mediated immunity. Moreover, it was revealed that octa-, deca-, and dodeca-β-glucans were much more immunogenic than the hexamer and that the octamer was the best among these. The results suggested that the optimal oligosaccharide sequence of β-glucan required for exceptional immunogenicity was a hepta- or octamer and that longer glucans are not necessarily better antigens, a finding that may be of general importance. Most importantly, the octa-β-glucan-KLH conjugate provoked protective immunity against Candida albicans infection in a systemic challenge model in mice, suggesting the great potential of this glycoconjugate as a clinically useful immunoprophylactic antifungal vaccine. (Chemical Equation Presented).
TMSOTf-catalyzed silylation: Streamlined regioselective one-pot protection and acetylation of carbohydrates
Joseph, A. Abragam,Verma, Ved Prakash,Liu, Xin-Yi,Wu, Chia-Hui,Dhurandhare, Vijay M.,Wang, Cheng-Chung
experimental part, p. 744 - 753 (2012/03/11)
A highly efficient TMSOTf-catalyzed HMDS silylation of sugars, which can easily be integrated with subsequent reactions in one-pot fashion, has been developed. Its usefulness was demonstrated by applications to streamlined regioselective one-pot protection and nonenzymatic acetylation of unprotected sugars. Monosaccharide and trehalose building blocks with orthogonally well-differentiated hydroxy groups were efficiently prepared starting with free sugars in one-pot fashion without the need for prior per-O-silylation. Regioselectively protected and acetylated building blocks were prepared directly from unprotected sugars in a one-pot manner involving up to five TMSOTf-catalyzed reactions, including a new TMSOTf-catalyzed silylation of carbohydrates. Copyright
