Effect of Azide Position on the Rate of Azido Glucose–Cyclooctyne Cycloaddition

Stewart, Jessica A.; Wilson, Cody James; Swarts, Benjamin M.

doi:10.1080/07328303.2014.931963

Cited by 3 publications

(3 citation statements)

References 36 publications

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“…Synthesis. Reaction between the equivalent amounts of 8azidoadenosine 59 1 and symmetrically fused cyclopropyl cyclooctyne 10 (OCT) 5 occurred efficiently in an aqueous solution of acetonitrile (ACN) at ambient temperature (3 h) to produce triazole 7 in 96% yield as a mixture 60 of ∼1:1 regioisomers after silica gel chromatography or HPLC purification (Scheme 1). This reaction time and efficiency were similar when coupling of 1 and 5 was carried out in MeOH, EtOH, or Opti-MEM I cell culture media (see Table S1 in SI for reaction details).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging

Zayas¹,

Annoual²,

Das³

et al. 2015

Bioconjugate Chem.

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Strain-promoted click chemistry of nucleosides and nucleotides with an azido group directly attached to the purine and pyrimidine rings with various cyclooctynes in aqueous solution at ambient temperature resulted in efficient formation (3 min - 3 h) of fluorescent, light-up, triazole products. The 2- and 8-azidoadenine nucleosides reacted with fused cyclopropyl cyclooctyne, dibenzylcyclooctyne or monofluorocyclooctyne to produce click products functionalized with hydroxyl, amino, N-hydroxysuccinimide, or biotin moieties. The 5-azidouridine and 5-azido-2′-deoxyuridine were similarly converted to the analogous triazole products in quantitative yields in less than 5 minutes. The 8-azido-ATP quantitatively afforded the triazole product with fused cyclopropyl cyclooctyne in aqueous acetonitrile (3 h). The novel triazole adducts at the 2 or 8 position of adenine or 5-position of uracil rings induce fluorescence properties which were used for direct imaging in MCF-7 cancer cells without the need for traditional fluorogenic reporters. FLIM of the triazole click adducts demonstrated their potential utility for dynamic measuring and tracking of signaling events inside single living cancer cells.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging

Zayas¹,

Annoual²,

Das³

et al. 2015

Bioconjugate Chem.

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“…We envisioned GDL derivatives with an azido-handle (Scheme 1). Because of 6-azido-6-deoxy-glucose being most SPAACreactive [25] , and reports of in vivo 6-phosphogluconoylation [14] , we presumed that 6-substitution may maximize click chemistry accessibility, whilst least affecting lactone reactivity. We used Shvo's catalyst for oxidation.…”

Section: Azidogluconoylationmentioning

confidence: 99%

N‐Terminal Modification of Gly‐His‐Tagged Proteins with Azidogluconolactone

Brune

Lieknina

Sutov³

et al. 2021

ChemBioChem

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Site-specific protein modifications are vital for biopharmaceutical drug development. Gluconoylation is a nonenzymatic, post-translational modification of N-terminal HisTags. We report high-yield, site-selective in vitro α-aminoacylation of peptides, glycoproteins, antibodies, and Virus-like particles (VLPs) with azidogluconolactone at pH 7.5 in 1 h. Conjugates slowly hydrolyse, but diol-masking with borate esters inhibits reversibility. In an example, we multimerise azidogluconoylated SARS-CoV-2 receptor-binding domain (RBD) onto VLPs via click-chemistry, to give a COVID-19 vaccine. Compared to yeast antigen, HEK-derived RBD was immunologically superior, likely due to observed differences in glycosylation. We show the benefits of ordered over randomly oriented multimeric antigen display, by demonstrating single-shot seroconversion and best virus-neutralizing antibodies. Azidogluconoylation is simple, fast and robust chemistry, and should accelerate research and development.

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“…BCN-DAz-Biotin is based on the azide-reactive cyclooctyne bicyclo[6.1.0]nonyne (BCN), which can be can be readily synthesized (or obtained commercially) and is among the faster cyclooctynes for SPAAC. 13,14 The diazirine group was chosen as the photocrosslinker, and biotin was chosen as the affinity handle to allow either detection or enrichment using avidin products.…”

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confidence: 99%