Chemical Synthesis of a Heparan Sulfate Glycopeptide: Syndecan‐1

Yang, Bo; Yoshida, Keisuke; Yin, Zhaojun; Dai, Hang; Kavunja, Herbert W.; El-Dakdouki, Mohammad H.; Sungsuwan, Suttipun; Dulaney, Steven B.; Huang, Xuefei

doi:10.1002/ange.201205601

Cited by 14 publications

(4 citation statements)

References 68 publications

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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%

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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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Section: Application Of Preactivation Strategy In the Assembly Of Olimentioning

confidence: 99%

“…After that, syndecan‐1 which is a heparan sulfate glycopeptide consisting of heparan sulfate, a tetrasaccharide linker and a peptide, was synthesized successfully using the same strategy. [ 48 ]…”

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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“…To understand the structure-activity relationships of the sulfation patterns in HS, Seeberger, 4,5 Linhardt, 6,7 Liu, 8,9 Boons, 10,11 Weigel, 12 DeAngelis, 13 Hung, 14, 15 Huang, [16][17][18] and others [19][20][21][22][23][24] have developed chemical and chemoenzymatic synthetic approaches to well-dened HS oligosaccharides that have signicantly advanced our understanding of HS biology. Nevertheless, the chemical synthesis of HS oligosaccharides oen requires exquisite synthetic route design and skillful carbohydrate chemistry manipulations, resulting in high production cost and scalability challenges.…”

Section: Introductionmentioning

confidence: 99%

Heparan sulfate glycomimeticsviaiterative assembly of “clickable” disaccharides

Yang

Wang

et al. 2023

Chem. Sci.

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“…To understand the structure-activity relationships of the sulfation patterns in HS, Seeberger, [6,7,8] Linhardt, [9,10,11] Liu, [12,13,14] Boons, [15,16] Weigel, [17,18] DeAngelis, [19,20] Hung, [21,22,23] Huang, [24,25,26,27] and others [28,29,30,31,32,33,34] have developed chemical and chemoenzymatic synthetic approaches to welldefined HS oligosaccharides that have significantly advanced our understanding of HS biology. Nevertheless, the chemical synthesis of HS oligosaccharides often requires exquisite synthetic route design and skillful carbohydrate chemistry manipulations, resulting in high production cost and scalability challenges.…”

Section: Introductionmentioning

confidence: 99%

Heparan Sulfate Glycomimetics via Iterative Assembly of “Clickable” Disaccharides

Yang

Wang

et al. 2022

Preprint

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Heparan sulfate (HS) glycosaminoglycans are widely expressed on the mammalian cell surfaces and extracellular matrices and play important roles in variety of cell functions. Studies on the structure-activity relationships of HS have long been hampered by the challenges in obtaining chemically defined HS structures with unique sulfation patterns. Here, we report a new approach to HS glycomimetics based on iterative assembly of clickable disaccharide building blocks that mimic the disaccharide repeating units of native HS. Variably sulfated clickable disaccharides were facilely assembled into a library of mass spec-sequencible HS-mimetic oligomers with defined sulfation patterns by solution-phase and solid-phase iterative syntheses. Microarray and surface plasmon resonance (SPR) binding assays corroborated with the molecular dynamic (MD) simulation and confirmed that these HS-mimetic oligomers bind protein fibroblast growth factor 2 (FGF-2) in a sulfation-dependent manner consistent with that of the native HS. This work established a general approach to HS glycomimetics that can potentially serve as alternatives to native HS in both fundamental research and disease models.

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Chemical Synthesis of a Heparan Sulfate Glycopeptide: Syndecan‐1

Cited by 14 publications

References 68 publications

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

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

Heparan sulfate glycomimeticsviaiterative assembly of “clickable” disaccharides

Heparan Sulfate Glycomimetics via Iterative Assembly of “Clickable” Disaccharides

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