Modification of the C3-Position of 2,3-Dehydro-2-deoxy-N-acetylneuraminic Acid with An Acetic Acid Equivalent

Keiya Uezono; Risa Maeda; Makoto Yoritate; Hiroaki Matoba; Go Hirai

doi:10.1246/cl.220507

Modification of the C3-Position of 2,3-Dehydro-2-deoxy-N-acetylneuraminic Acid with An Acetic Acid Equivalent

Keiya Uezono, Risa Maeda, Makoto Yoritate, Hiroaki Matoba, Go Hirai

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

Direct modification at the C-3 position of 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (DANA) derivatives with malonates has been achieved by means of Mn(OAc)3-mediated oxidative coupling reaction, giving C3-modified DANA derivatives in good yield with high diastereo-selectivity. We also designed and synthesized 3-CH2COOH-DANA as a candidate sialidase inhibitor, but found that its inhibitory activity towards several sialidases was weak, possibly because the acidic functional group is located too close to the DANA skeleton.

Original language	English
Pages (from-to)	71-74
Number of pages	4
Journal	Chemistry Letters
Volume	52
Issue number	2
DOIs	https://doi.org/10.1246/cl.220507
Publication status	Published - Feb 2023

All Science Journal Classification (ASJC) codes

General Chemistry

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abstract = "Direct modification at the C-3 position of 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (DANA) derivatives with malonates has been achieved by means of Mn(OAc)3-mediated oxidative coupling reaction, giving C3-modified DANA derivatives in good yield with high diastereo-selectivity. We also designed and synthesized 3-CH2COOH-DANA as a candidate sialidase inhibitor, but found that its inhibitory activity towards several sialidases was weak, possibly because the acidic functional group is located too close to the DANA skeleton.",

author = "Keiya Uezono and Risa Maeda and Makoto Yoritate and Hiroaki Matoba and Go Hirai",

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AU - Maeda, Risa

AU - Yoritate, Makoto

AU - Matoba, Hiroaki

AU - Hirai, Go

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N2 - Direct modification at the C-3 position of 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (DANA) derivatives with malonates has been achieved by means of Mn(OAc)3-mediated oxidative coupling reaction, giving C3-modified DANA derivatives in good yield with high diastereo-selectivity. We also designed and synthesized 3-CH2COOH-DANA as a candidate sialidase inhibitor, but found that its inhibitory activity towards several sialidases was weak, possibly because the acidic functional group is located too close to the DANA skeleton.

AB - Direct modification at the C-3 position of 2,3-dehydro-2-deoxy-N-acetylneuraminic acid (DANA) derivatives with malonates has been achieved by means of Mn(OAc)3-mediated oxidative coupling reaction, giving C3-modified DANA derivatives in good yield with high diastereo-selectivity. We also designed and synthesized 3-CH2COOH-DANA as a candidate sialidase inhibitor, but found that its inhibitory activity towards several sialidases was weak, possibly because the acidic functional group is located too close to the DANA skeleton.

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Modification of the C3-Position of 2,3-Dehydro-2-deoxy-N-acetylneuraminic Acid with An Acetic Acid Equivalent

Abstract

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