Automated Glycan Assembly in a Variable-Bed Flow Reactor Provides Insights into Oligosaccharide–Resin Interactions

Sletten, Eric T.; Danglad‐Flores, José; Nuño, Manuel; Guthrie, Duncan; Seeberger, Peter H.

doi:10.1021/acs.orglett.0c01264

Cited by 12 publications

(13 citation statements)

References 18 publications

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“…In 2020, Seeberger and coworkers incorporated a variable‐bed flow reactor (VBFR) into a fully automated flow system for automated glycan assembly (Figure 5d). [ 43 ] By employing an autosampler and two Vapourtec R‐series pump modules for reagent delivery, the AGA‐VBFR system is capable of tracking the resin growth patterns in real time, thereby allowing for calculation of the on‐resin solvation state of each monosaccharide. As demonstrated in the synthesis of oligomannosides, this synthesizer could monitor the coupling efficiencies for each step of the AGA cycle.…”

Section: Automated Glycan Assemblymentioning

confidence: 99%

Automated Chemical Solid‐Phase Synthesis of Glycans

Yang

2022

Chin. J. Chem.

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Automated chemical solid-phase synthesis is an automation platform for rapid and reliable synthesis of glycans. Since the seminal work of Automated Glycan Assembly (AGA) disclosed by Seeberger in 2001, AGA has evolved from a proof-of-concept to a robust and reliable technology for streamlined production of various types of glycans. Through more than 20 years of unceasing efforts, the major breakthroughs in AGA including linkers, approved building blocks, and synthesizers have been acquired, and numerous influential achievements have been made in complex glycan synthesis. In addition, the HPLC-assisted automated synthesis emerges as a promising automation platform to access glycans. In this review, we highlight the key advances in the field of automated chemical solid-phase synthesis, especially in AGA. The synthesis of representative glycans based on AGA is also described.

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Section: Automated Glycan Assemblymentioning

confidence: 99%

Automated Chemical Solid‐Phase Synthesis of Glycans

Yang

2022

Chin. J. Chem.

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“…The oligosaccharide is then cleaved by ultraviolet (UV)-irradiation, while quality control is carried out by HPLC, MS, and NMR. Recent advances in AGA quality control allowed real-time monitoring of reaction cycles and may improve the platform's efficiency further, preparing it for commercial-scale production of high-quality oligosaccharides [77].…”

Section: Cell-free Harvesting Of O-sp Through Chemical Synthesismentioning

confidence: 99%

Recent advances in lipopolysaccharide-based glycoconjugate vaccines

Zhu

Rollier

Pollard

2021

Expert Review of Vaccines

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Introduction:The public health burden caused by pathogenic Gram-negative bacteria is increasingly prominent due to antimicrobial resistance. The surface carbohydrates are potential antigens for vaccines against Gram-negative bacteria. The enhanced immunogenicity of the O-specific polysaccharide (O-SP) moiety of LPS when coupled to a carrier protein may protect against bacterial pathogens. However, because of the toxic lipid A moiety and relatively high costs of O-SP isolation, LPS has not been a popular vaccine antigen until recently. Areas covered: In this review, we discuss the rationales for developing LPS-based glycoconjugate vaccines, principles of glycoconjugate-induced immunity, and highlight the recent developments and challenges faced by LPS-based glycoconjugate vaccines. Expert opinion: Advances in LPS harvesting, LPS chemical synthesis, and newer carrier proteins in the past decade have propelled LPS-based glycoconjugate vaccines toward further development, through to clinical evaluation. The development of LPS-based glycoconjugates offers a new horizon for vaccine prevention of Gram-negative bacterial infection.

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Section: Introductionmentioning

confidence: 99%

“…Flow-based SPPS systems have gained much attention in the last decades as they allow automation and acceleration of the process. − This methodology relies on the flow of reagent through the solid support with high convective mass transfer. This approach can be used with or without heating. − An automated flow-based setup for SPPS (AFPS) presented an extremely fast strategy for synthesizing peptides and proteins (Figure A). AFPS relies on elevated temperatures for accelerating coupling and deprotection reactions, and a full introduction cycle of each amino acid can be accomplished in 40 s. ,, In AFPS, the solid support is stationary and a large excess of reagents (3–60 equiv) is used for coupling, proving that elevated temperature and flow-based mixing only partially suffice when short reaction times are employed.…”

Section: Introductionmentioning

confidence: 99%

Stirring Peptide Synthesis to a New Level of Efficiency

Naoum

Alshanski

Mayer

et al. 2022

Org. Process Res. Dev.

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Accelerating solid-phase synthesis is crucial for accessing a large number of peptides in a short time. Since standard peptide synthesis is usually done under poor diffusion conditions with slow or no mixing of the solid support, acceleration of the process is achieved by applying a large excess of reagents. In this work, overhead stirring and heating were combined to provide accelerated solid-phase peptide synthesis without using an excess of reagent. A new setup that allows both heating and fast stirring was designed specifically for research laboratory-scale peptide synthesis. By increasing the diffusion of both reagents and beads in a narrow dimension reactor, solid-phase reactions were done in seconds and medium-size peptides were synthesized in minutes.

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Automated Glycan Assembly in a Variable-Bed Flow Reactor Provides Insights into Oligosaccharide–Resin Interactions

Cited by 12 publications

References 18 publications

Automated Chemical Solid‐Phase Synthesis of Glycans

Automated Chemical Solid‐Phase Synthesis of Glycans

Recent advances in lipopolysaccharide-based glycoconjugate vaccines

Stirring Peptide Synthesis to a New Level of Efficiency

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