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一种适用于合成I环修饰的4,5-2-脱氧链霉胺型氨基糖苷类抗生素的假二糖的合成。

Synthesis of a Pseudodisaccharide Suitable for Synthesis of Ring I Modified 4,5-2-Deoxystreptamine Type Aminoglycoside Antibiotics.

作者信息

Sonousi Amr, Vasella Andrea, Crich David

机构信息

Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States.

Organic Chemistry Laboratory, ETH Zürich, Vladimir-Prelog-Weg 1-5/10, 8093 Zürich, Switzerland.

出版信息

J Org Chem. 2020 Jun 5;85(11):7583-7587. doi: 10.1021/acs.joc.0c00743. Epub 2020 May 8.

DOI:10.1021/acs.joc.0c00743
PMID:32336094
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7275914/
Abstract

To facilitate the synthesis of paromomycin and/or neomycin analogues, we describe a cleavage of ring I from paromomycin that proceeds in the presence of azides and affords a glycosyl acceptor for the installation of a modified ring I. A paromomycin 4',6'-diol is oxidized by the Dess-Martin periodinane followed by -chloroperoxybenzoic acid. Base treatment then affords a protected pseudodisaccharide, which functions as a glycosyl acceptor. The method should also apply to the cleavage of pyranosyl 4,6-diols from oligosaccharides and glycoconjugates.

摘要

为了促进巴龙霉素和/或新霉素类似物的合成，我们描述了一种从巴龙霉素中裂解I环的方法，该方法在叠氮化物存在下进行，并提供用于安装修饰I环的糖基受体。巴龙霉素4',6'-二醇先被戴斯-马丁高碘烷氧化，然后用间氯过氧苯甲酸处理。碱处理后得到一种受保护的假二糖，它可作为糖基受体。该方法也应适用于从寡糖和糖缀合物中裂解吡喃糖基4,6-二醇。

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Synthesis of a Pseudodisaccharide Suitable for Synthesis of Ring I Modified 4,5-2-Deoxystreptamine Type Aminoglycoside Antibiotics.一种适用于合成I环修饰的4,5-2-脱氧链霉胺型氨基糖苷类抗生素的假二糖的合成。
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本文引用的文献

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Aminoglycosides: Time for the Resurrection of a Neglected Class of Antibacterials?氨基糖苷类药物：被忽视的抗菌药物类别的复兴时机？
ACS Infect Dis. 2020 Feb 14;6(2):168-172. doi: 10.1021/acsinfecdis.9b00441. Epub 2019 Dec 19.
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Modification at the 2'-Position of the 4,5-Series of 2-Deoxystreptamine Aminoglycoside Antibiotics To Resist Aminoglycoside Modifying Enzymes and Increase Ribosomal Target Selectivity.对4,5-系列2-脱氧链霉胺氨基糖苷类抗生素2'-位进行修饰以抵抗氨基糖苷类修饰酶并提高核糖体靶点选择性
ACS Infect Dis. 2019 Oct 11;5(10):1718-1730. doi: 10.1021/acsinfecdis.9b00128. Epub 2019 Sep 13.
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Synthesis of Ring II/III Fragment of Kanamycin: A New Minimum Structural Motif for Aminoglycoside Recognition.卡那霉素II/III环片段的合成：氨基糖苷识别的一种新的最小结构基序
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Design, Multigram Synthesis, and in Vitro and in Vivo Evaluation of Propylamycin: A Semisynthetic 4,5-Deoxystreptamine Class Aminoglycoside for the Treatment of Drug-Resistant Enterobacteriaceae and Other Gram-Negative Pathogens.丙氨霉素的设计、多克合成、体外和体内评价：一种用于治疗耐药肠杆菌科和其他革兰氏阴性病原体的半合成 4,5-去氧链霉胺类氨基糖苷类药物。
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EcoSal Plus. 2018 Nov;8(1). doi: 10.1128/ecosalplus.ESP-0002-2018.
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