Synthesis of Neu5Gc2en (DANA-Gc) Derivative

Neu5Gc2en (DANA-Gc) was synthesized as previously published^{42 (link)-45 (link)} with minor modifications. Briefly, Neu5Gc (Sigma-Aldrich) was treated with Dowex 50W-X8 (H+) resin in MeOH for 20 hours at 20 °C to form the methyl ester. This ester was then treated with acetic anhydride and pyridine for 42 h at 20 °C to generate the peracetylated methyl ester, which was purified by column chromatography (50:l CHCl₃- MeOH). This sample was treated with TMSOTf under dry nitrogen at 0 °C in MeCN for 6 h to induce elimination. The unsaturated compound was purified by chromatography (toluene/acetone, 3:1 → 2:1). The acetyl groups were cleaved by treatment with NaOH in MeOH over 12 hours followed by neutralization with H+ resin.

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Zaramela L.S., Martino C., Alisson-Silva F., Rees S.D., Diaz S.L., Chuzel L., Ganatra M.B., Taron C.H., Secrest P., Zuñiga C., Huang J., Siegel D., Chang G., Varki A, & Zengler K. (2019). Gut bacteria responding to dietary change encode sialidases that exhibit preference for red meat-associated carbohydrates. Nature microbiology, 4(12), 2082-2089.

Publication 2019

Neu5Gc

Acetic anhydride Acetone Chcl3 Chromatography Dowex Ester Nitrogen Pyridine Resin Toluene

Corresponding Organization : University of California, San Diego

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Variable analysis

independent variables

Treatment of Neu5Gc with Dowex 50W-X8 (H+) resin in MeOH for 20 hours at 20 °C
Treatment of the methyl ester with acetic anhydride and pyridine for 42 h at 20 °C
Treatment of the peracetylated methyl ester with TMSOTf under dry nitrogen at 0 °C in MeCN for 6 h
Treatment of the unsaturated compound with NaOH in MeOH over 12 hours

dependent variables

Formation of the methyl ester
Formation of the peracetylated methyl ester
Formation of the unsaturated compound
Cleavage of the acetyl groups

control variables

Reaction time
Reaction temperature
Reaction solvents

controls

Neu5Gc (Sigma-Aldrich) as a source material

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