A facile microwave-assisted protocol for rapid synthesis of N-acetylneuraminic acid congeners

Saludes, Jonel P.; Sahoo, Dhananjaya; Monreal, I. Abrrey

doi:10.1039/c3nj01459b

Cited by 8 publications

(8 citation statements)

References 28 publications

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“…1 H NMR spectrum was recorded in CDCl 3 and is consistent with literature. 14 MALDI-TOF-MS m / z : calcd for C 22 H 31 NO 14 Na + , 556.1642; found, 556.2092 and calcd for C 22 H 31 NO 14 K + , 572.1382; found, 572.1739.…”

Section: Methodsmentioning

confidence: 99%

“…We also found the 1 H NMR spectra of 3 and 9 to be consistent with literature. 14,28 The identity of 12 was confirmed by a combination of MS and 2D-NMR (COSY and NOESY, Fig. S10-S11).…”

mentioning

confidence: 85%

“…The sugar (0.05 g, 0.16 mmol) was treated with 1.0 mL MeOH and SSA (0.1 – 1.0 eq., Table S1, Supplementary Information) followed by microwave-assisted heating at variable power and a fixed temperature of 80 °C for 30 min 14 using Biotage Initiator + SP Wave reactor (Scheme 1, i ). Completion of the reaction was monitored by thin layer chromatography (TLC) using 3:1 CH 2 Cl 2 -MeOH and the disappearance of starting material and formation of 2 (R f = 0.36), which indicated complete consumption of 1 after 30 min.…”

mentioning

confidence: 99%

“…The formation of 5 is not surprising since it was previously found as a minor product during esterification of 1 under microwave irradiation conditions. 15,14 In an attempt to further optimize this reaction, we varied both the reaction temperature (60 – 100 °C) and time (20 – 30 min), but found the above-mentioned conditions sufficient and optimal (Tables S2 and S3). We translated this protocol to the gram scale synthesis of 2 at 97% isolated yield after column chromatography.…”

mentioning

confidence: 99%

“…To test our hypothesis that SSA can catalyze the β-elimination at C-2, we investigated the direct synthesis of 9 from 2 using our previous microwave-assisted peracetylation conditions as starting point. 14 A mixture of 2 (0.05 g, 0.16 mmol) and SSA (0.05 g, 0.16 mmol, 1 eq.) was treated with excess Ac 2 O (6.6 mmol, 40 eq.)…”

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confidence: 99%

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One-pot SSA-catalyzed β-elimination: an efficient and inexpensive protocol for easy access to the glycal of sialic acid

Paragas

Monreal

Vasil

et al. 2015

Carbohydrate Research

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Neu5Ac2en1Me per-OAc, the fully protected glycal of sialic acid, is a key intermediate in the discovery of therapeutics and diagnostics, including anti-influenza drugs and proteolysis resistant peptidomimetic foldamers. The synthesis of this sialic acid derivative, however, still relies on standard sugar chemistry that utilizes multi-step methodologies. Herein we report a facile and highly efficient microwave-assisted preparation of Neu5Ac1Me using silica sulfuric acid (SSA) as solid-supported acid catalyst that is one- to two-orders of magnitude faster than standard procedures. We also describe the microwave-assisted and SSA-catalyzed one-pot, rapid, solvent free reaction that combines both peracetylation and β-elimination reactions in one step to generate the glycal from Neu5Ac1Me. We coined the term One-pot SSA-catalyzed Technology for β-Elimination Protocol (OneSTEP) to describe this least laborious, most efficient, and practical preparation to date of Neu5Ac2en1Me per-OAc in terms of yield, time, reagent cost, and waste generation.

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Section: Methodsmentioning

confidence: 99%

“…We also found the 1 H NMR spectra of 3 and 9 to be consistent with literature. 14,28 The identity of 12 was confirmed by a combination of MS and 2D-NMR (COSY and NOESY, Fig. S10-S11).…”

mentioning

confidence: 85%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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One-pot SSA-catalyzed β-elimination: an efficient and inexpensive protocol for easy access to the glycal of sialic acid

Paragas

Monreal

Vasil

et al. 2015

Carbohydrate Research

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Synthesis and Thermodynamic Evaluation of Sialyl‐Tn MUC1 Glycopeptides Binding to Macrophage Galactose‐Type Lectin

Ayyalasomayajula,

Boneva,

Ormaza

et al. 2024

ChemBioChem

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Interactions between the tumor‐associated carbohydrate antigens of Mucin 1 (MUC1) and the carbohydrate‐binding proteins, lectins, often lead to the creation of a pro‐tumor microenvironment favoring tumor initiation, progression, metastasis, and immune evasion. Macrophage galactose binding lectin (MGL) is a C‐type lectin receptor found on antigen‐presenting cells that facilitates the uptake of carbohydrate antigens for antigen presentation, modulating the immune response homeostasis, autoimmunity, and cancer. Considering the crucial role of tumor‐associated forms of MUC1 and MGL in tumor immunology, a thorough understanding of their binding interaction is essential for it to be exploited for cancer vaccine strategies. The synthesis of MUC1 glycopeptide models carrying a single or multiple Tn and/or sialyl‐Tn antigen(s) is described. A novel approach for the sialyl‐Tn threonine building block suitable for the solid phase peptide synthesis was developed. The thermodynamic profile of the binding interaction between the human MGL and MUC1 glycopeptide models was analyzed using isothermal titration calorimetry. The measured dissociation constants for the sialyl‐Tn‐bearing peptide epitopes were consistently lower compared to the Tn antigen and ranged from 10 μM for mono‐ to 100 nM for triglycosylated MUC1 peptide, respectively. All studied interactions, regardless of the glycan’s site of attachment or density, exhibited enthalpy‐driven thermodynamics.

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Efficient Microwave‐Assisted Synthesis of Sonogashira‐Coupled Perylene Monoimide Derivatives: Impact of Electron‐Donating Groups on Optoelectronic Properties

et al. 2017

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An efficient microwave‐assisted Sonogashira‐coupling protocol for the synthesis of peri‐functionalized perylene monoimide dye derivatives was developed. This method was found to be significantly faster than the conventional coupling method and provided products with interesting optoelectronic properties in moderate to good yields. Electronic communication of the electron‐rich aryl and polyaryl groups with the perylene core through C≡C bonds was investigated.

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A facile microwave-assisted protocol for rapid synthesis of N-acetylneuraminic acid congeners

Cited by 8 publications

References 28 publications

One-pot SSA-catalyzed β-elimination: an efficient and inexpensive protocol for easy access to the glycal of sialic acid

One-pot SSA-catalyzed β-elimination: an efficient and inexpensive protocol for easy access to the glycal of sialic acid

Synthesis and Thermodynamic Evaluation of Sialyl‐Tn MUC1 Glycopeptides Binding to Macrophage Galactose‐Type Lectin

Efficient Microwave‐Assisted Synthesis of Sonogashira‐Coupled Perylene Monoimide Derivatives: Impact of Electron‐Donating Groups on Optoelectronic Properties

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