Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers

Jaipuri, Firoz A.; Pohl, Nicola L. B.

doi:10.1039/b803451f

Cited by 124 publications

(88 citation statements)

References 82 publications

(7 reference statements)

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“…carboxymethyl-α- d -mannopyranosyl-(1,2)- d -mannopyranoside was synthesized using an alkenyl fluorous tag as previously reported [43]. Fluorous solid phase extraction (FSPE) was used to purify all the intermediates [44–46].…”

Section: Methodsmentioning

confidence: 99%

Carbohydrate-functionalized nanovaccines preserve HIV-1 antigen stability and activate antigen presenting cells

Ramirez

Roychoudhury

Habte

et al. 2014

Journal of Biomaterials Science, Polymer Edition

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The functionalization of polymeric nanoparticles with ligands that target specific receptors on immune cells offers the opportunity to tailor adjuvant properties by conferring pathogen mimicking attributes to the particles. Polyanhydride nanoparticles are promising vaccine adjuvants with desirable characteristics such as immunomodulation, sustained antigen release, activation of antigen presenting cells, and stabilization of protein antigens. These capabilities can be exploited to design nanovaccines against viral pathogens, such as HIV-1, due to the important role of dendritic cells and macrophages in viral spread. In this work, an optimized process was developed for carbohydrate functionalization of HIV-1 antigen-loaded polyanhydride nanoparticles. The carbohydrate-functionalized nanoparticles preserved antigenic properties upon release and also enabled sustained antigen release kinetics. Particle internalization was observed to be chemistry-dependent with positively charged nanoparticles being taken up more efficiently by dendritic cells. Up-regulation of the activation makers CD40 and CD206 was demonstrated with carboxymethyl-α-d-mannopyranosyl-(1,2)-d-mannopyranoside functionalized nanoparticles. The secretion of the cytokines IL-6 and TNF-α was shown to be chemistry-dependent upon stimulation with carbohydrate-functionalized nanoparticles. These results offer important new insights upon the interactions between carbohydrate-functionalized nanoparticles and antigen presenting cells and provide foundational information for the rational design of targeted nanovaccines against HIV-1.

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Section: Methodsmentioning

confidence: 99%

Carbohydrate-functionalized nanovaccines preserve HIV-1 antigen stability and activate antigen presenting cells

Ramirez

Roychoudhury

Habte

et al. 2014

Journal of Biomaterials Science, Polymer Edition

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“…Recently, Pohl and co-workers employed this technology to synthesize tetra-and penta-mannose oligosaccharides by using a fluorous tag containing an oxygen spacer Glycoscience: Biology and Medicine DOI 10.1007/978-4-431-54836-2_34-1 # Springer Japan 2014 ( Fig. 2) (Jaipuri and Pohl 2008). This particular fluorous linker significantly increased the solubility of oligosaccharides and the fluorous tag in organic solvents used in glycosylations.…”

Section: Automated Solution-phase Oligosaccharide Synthesismentioning

confidence: 98%

Automation in Glycan Synthesis

Wong

2014

Glycoscience: Biology and Medicine

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Nucleic acids, proteins, and glycoconjugates, the three major marcomolucules, are key to the signal transduction processes in living organisms. Nucleic acids can be synthesized via chemical and biological methods with the aid of the polymerase chain reaction, and protein sequences, which are encoded by DNA, can therefore be easily determined, produced, and manipulated through recombinant DNA technology. In addition, automatic synthesizers are available for the synthesis of these linear polymers using a single protecting-group strategy in the iterative process. Saccharides, however, are often branched and made with a diverse set of enzymes. There is no information carrier that encodes a particular saccharide sequence. Traditional synthesis of saccharides requires multiple protection and deprotection steps and stereocontrol in each glycosylation reaction. Development of automatic saccharide synthesis can speed up the preparation of saccharides for study and thus facilitate the progression of glycoscience research.

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“…10.11) [138]. Their approach involved the use of a fluorous tag attached glycosidically to a glycosyl acceptor (54), which was glycosylated using excess of the trichloroacetimidate donor (53) in the presence of TMSOTf.…”

Section: Automation Of the Fluorous Tag-supported Synthesismentioning

confidence: 99%