A Convergent Synthesis of 6‐<i>O</i>‐Branched β‐Glucan Oligosaccharides

Liao, Guochao; Srinivas, Burgula; Zhou, Zhifang; Guo, Zhi‐Xin

doi:10.1002/ejoc.201500229

Cited by 20 publications

(18 citation statements)

References 27 publications

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“…The results obtained here and in a previous study 29 suggested that 1a – 3a elicited similar pattern and strength of immune responses as the KLH conjugate of an optimized linear oligo-β-glucan, i.e., octa-β-glucan. In the previous paper, we only reported the results with Titermax Gold as the adjuvant, but we also evaluated the linear oligo-β-glucan-KLH conjugates in the presence of CFA, which gave very similar results.…”

Section: Discussionsupporting

confidence: 84%

6-O-Branched Oligo-β-glucan-Based Antifungal Glycoconjugate Vaccines

et al. 2015

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With the rapid growth in fungal infections and drug-resistant fungal strains, antifungal vaccines have become an especially attractive strategy to tackle this important health problem. β-Glucans, a class of extracellular carbohydrate antigens abundantly and consistently expressed on fungal cell surfaces, are intriguing epitopes for antifungal vaccine development. β-Glucans have a conserved β-1,3-glucan backbone with sporadic β-1,3- or β-1,6-linked short glucans as branches at the 6-O-positions, and the branches may play a critical role in their immunologic functions. To study the immunologic properties of branched β-glucans and develop β-glucan-based antifungal vaccines, three branched β-glucan oligosaccharides with 6-O-linked β-1,6-tetraglucose, β-1,3-diglucose, and β-1,3-tetraglucose branches on a β-1,3-nonaglucan backbone, which mimic the structural epitopes of natural β-glucans, were synthesized and coupled with keyhole limpet hemocyanin (KLH) to form novel synthetic conjugate vaccines. These glycoconjugates were proved to elicit strong IgG antibody responses in mice. It was also discovered that the number, size, and structure of branches linked to the β-glucan backbone had a significant impact on the immunologic property. Moreover, antibodies induced by the synthetic oligosaccharide-KLH conjugates were able to recognize and bind to natural β-glucans and fungal cells. Most importantly, these conjugates elicited effective protection against systemic Candida albicans infection in mice. Thus, branched oligo-β-glucans were identified as functional epitopes for antifungal vaccine design and the corresponding protein conjugates as promising antifungal vaccine candidates.

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Section: Discussionsupporting

confidence: 84%

6-O-Branched Oligo-β-glucan-Based Antifungal Glycoconjugate Vaccines

et al. 2015

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“…In addition to Globo-H 105 and arabinogalactan 116 , other complex oligosaccharides obtained by the preactivation-based thioglycoside method include branched oligosaccharides from glycolipid family including Lewis X pentasaccharide 117 , dimeric Lewis X 118 [ 63 ], tristearoyl lipomannan 119 [ 64 ], gangliosides GM1 120 [ 65 ] and GM2 121 ( Fig. 5 ) [ 66 ], microbial glycans such as the heptasaccharide repeating unit of type V group B Streptococcus capsular polysaccharide 122 [ 67 ], β-glucan oligosaccharides 123 from fungal cells [ 68 – 69 ], oligomannan containing multiple challenging β-mannosyl linkages 124 [ 54 ] ( Fig. 6 ), chitotetraose [ 70 ], mammalian glycans including complex type bisected N-glycan dodecasaccharide 125 [ 71 ], glycosaminoglycans including hyaluronic acid oligosaccharides 126 [ 72 – 73 ] ( Fig.…”

Section: Reviewmentioning

confidence: 99%

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

Yang¹,

Yang²,

Ramadan³

et al. 2017

Beilstein J. Org. Chem.

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Most glycosylation reactions are performed by mixing the glycosyl donor and acceptor together followed by the addition of a promoter. While many oligosaccharides have been synthesized successfully using this premixed strategy, extensive protective group manipulation and aglycon adjustment often need to be performed on oligosaccharide intermediates, which lower the overall synthetic efficiency. Preactivation-based glycosylation refers to strategies where the glycosyl donor is activated by a promoter in the absence of an acceptor. The subsequent acceptor addition then leads to the formation of the glycoside product. As donor activation and glycosylation are carried out in two distinct steps, unique chemoselectivities can be obtained. Successful glycosylation can be performed independent of anomeric reactivities of the building blocks. In addition, one-pot protocols have been developed that have enabled multiple-step glycosylations in the same reaction flask without the need for intermediate purification. Complex glycans containing both 1,2-cis and 1,2-trans linkages, branched oligosaccharides, uronic acids, sialic acids, modifications such as sulfate esters and deoxy glycosides have been successfully synthesized. The preactivation-based chemoselective glycosylation is a powerful strategy for oligosaccharide assembly complementing the more traditional premixed method.

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“…Huang and Ye groups [ 10 ] firstly established the concept of preactivation‐based one‐pot glycosylation, which has been used for a large quantity of oligosaccharides and polysaccharides synthesis. [ 47‐58 ]…”

Section: Application Of Preactivation Strategy In the Assembly Of Olimentioning

confidence: 99%

Donor Preactivation‐Based Glycosylation: An Efficient Strategy for Glycan Synthesis

Qin

2021

Chin. J. Chem.

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Carbohydrates have gained a lot of appreciation in the past few decades due to their important roles in numerous biological events. Acquiring a structurally well‐defined carbohydrate compound is essential for the understanding of its functions. Although some innovative methods have been developed for the synthesis of complex oligosaccharides, glycan synthesis is in general still a time‐consuming and difficult work. Herein, we will introduce the preactivation‐based glycosylation strategy, which is an efficient protocol independent of the reactivity of glycosyl donor. This review will focus on summarizing the versatile applications of preactivation strategy in stereoselective glycosylation and one‐pot assembly of biologically important oligosaccharides and even polysaccharides. What is the most favorite and original chemistry developed in your research group? Preactivation‐based one‐pot glycosylation strategy and applications. How do you get into this specific field? Could you please share some experiences with our readers? I got into this field when I was a research associate in 1996. My supervisor, Prof. Chi‐Huey Wong, gave me a research topic for synthesis of oligosaccharide libraries. At that moment, as a beginner, I did not know too much carbohydrate chemistry, just to learn and to do it. The importance and challenge of carbohydrates attracted me. What is the most important personality for scientific research? Curiosity, passion, and creative thinking. How do you supervise your students? In my opinion, before the graduate students start a specific project, their experimental skills need to be well trained. During the period of graduate studies, the enhancement of abilities to analyze problems and to solve problems is very important. The graduate students should always keep an eye on the unusual experimental phenomena. What's your hobbies? Reading history books. What is your favorite journals? The journals publishing the latest research works in chemistry and medical science.

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A Convergent Synthesis of 6‐O‐Branched β‐Glucan Oligosaccharides

Cited by 20 publications

References 27 publications

6-O-Branched Oligo-β-glucan-Based Antifungal Glycoconjugate Vaccines

6-O-Branched Oligo-β-glucan-Based Antifungal Glycoconjugate Vaccines

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

Donor Preactivation‐Based Glycosylation: An Efficient Strategy for Glycan Synthesis

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