Synthesis of capuramycin and its analogues via a Ferrier-type I reaction and their biological evaluation

Shintaro Kusaka; Kazuki Yamamoto; Motoko Shinohara; Yusuke Minato; Satoshi Ichikawa

doi:10.1016/j.bmc.2022.117011

Synthesis of capuramycin and its analogues via a Ferrier-type I reaction and their biological evaluation

Shintaro Kusaka, Kazuki Yamamoto, Motoko Shinohara, Yusuke Minato, Satoshi Ichikawa

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

3 Citations (Scopus)

Abstract

The total synthesis of capuramycin (1), which is a promising anti-tubercular antibiotics, has been accomplished using Ferrier-type I reaction as a key step. This total synthesis is an alternative approach to the synthesis of capuramycin and its analogues. The 3′-O-demethyl analogue (2), which exhibits an equivalent antibacterial activity as capuramycin (1) against Mycobacterium smegmatis and Mycobacterium avium, is suggested to have potential as a lead structure of capuramycin analogues because 2 is more accessible from a synthetic view point.

Original language	English
Article number	117011
Journal	Bioorganic and Medicinal Chemistry
Volume	73
DOIs	https://doi.org/10.1016/j.bmc.2022.117011
Publication status	Published - 01-11-2022
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2022.117011

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abstract = "The total synthesis of capuramycin (1), which is a promising anti-tubercular antibiotics, has been accomplished using Ferrier-type I reaction as a key step. This total synthesis is an alternative approach to the synthesis of capuramycin and its analogues. The 3′-O-demethyl analogue (2), which exhibits an equivalent antibacterial activity as capuramycin (1) against Mycobacterium smegmatis and Mycobacterium avium, is suggested to have potential as a lead structure of capuramycin analogues because 2 is more accessible from a synthetic view point.",

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author = "Shintaro Kusaka and Kazuki Yamamoto and Motoko Shinohara and Yusuke Minato and Satoshi Ichikawa",

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AU - Kusaka, Shintaro

AU - Yamamoto, Kazuki

AU - Shinohara, Motoko

AU - Minato, Yusuke

AU - Ichikawa, Satoshi

PY - 2022/11/1

Y1 - 2022/11/1

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AB - The total synthesis of capuramycin (1), which is a promising anti-tubercular antibiotics, has been accomplished using Ferrier-type I reaction as a key step. This total synthesis is an alternative approach to the synthesis of capuramycin and its analogues. The 3′-O-demethyl analogue (2), which exhibits an equivalent antibacterial activity as capuramycin (1) against Mycobacterium smegmatis and Mycobacterium avium, is suggested to have potential as a lead structure of capuramycin analogues because 2 is more accessible from a synthetic view point.

KW - Antibacterial

KW - MraY

KW - Natural product

KW - Nucleoside

KW - Structure-activity relationship

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AN - SCOPUS:85139012026

SN - 0968-0896

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JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

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ER -

Synthesis of capuramycin and its analogues via a Ferrier-type I reaction and their biological evaluation

Abstract

All Science Journal Classification (ASJC) codes

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