Evidence map›Paper›PMID 40229233›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025

Total Synthesis of Kanamycins.

Kanae Hosomi, Banjo Imai, Naoto Takemura, Kazuki Senoo, Chigusa Hayashi, Masayuki Igarashi, Kazunobu Toshima, Daisuke Takahashi

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it
0cells of the map it votes in
0citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

0 citing papers in PubMed.

No citing paper in PubMed yet.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

8 authors.

Kanae HosomiDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Banjo ImaiDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Naoto TakemuraDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Kazuki SenooDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Chigusa HayashiInstitute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo, 141-0021, Japan.
Masayuki IgarashiInstitute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo, 141-0021, Japan.
Kazunobu ToshimaDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.ORCID https://orcid.org/0000-0003-3994-9099
Daisuke TakahashiDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.ORCID https://orcid.org/0000-0003-3222-6648

Funding

AMED-CREST JP22gm1610010JSPS KAKENHI JP23H01966Scientific Research (B); JST CREST JPMJCR20R3
6 · The paper itself

Abstract

Structurally modified aminoglycosides, such as kanamycin, have shown promise as antibiotics and premature termination codon read-through drugs to fight against drug-resistant bacteria and to treat genetic diseases, respectively. Therefore, research on developing and discovering aminoglycoside antibiotics has recently increased. However, synthetic strategies for controllably positioning the two 1,2-cis-glycoside moieties on the symmetrical structure of kanamycin have not yet been established. Herein, we report on a novel route for the total synthesis of kanamycins A and B via regio- and stereoselective introduction of 1,2-cis-glycosidic linkages as the key step. We successfully synthesized α(1,6)-linked glycoside using a 1,2-anhydro donor and 2-deoxy-myo-inositol 1,3,5-orthoformate acceptor in the presence of a boronic acid catalyst via desymmetric boron-mediated aglycon delivery. In addition, we also synthesized α(1,4)-linked glycoside using its corresponding trichloroacetimidate donor.

Indexed as

Anti-Bacterial AgentsKanamycinBoronic AcidsCatalysisGlycosidesStereoisomerismAnti-Bacterial AgentsBoronic AcidsGlycosidesKanamycinboron‐mediated aglycon deliverydesymmetrizationglycosylationkanamycintotal synthesis

Identifiers

PMID40229233
PMCPMC12238912

What OpenQuestion holds

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.