Total synthesis of siomycin A

Mori, Takeo; Higashibayashi, Shuhei; Goto, Taiji; Kohno, Mitsunori; Satouchi, Yukiko; Shinko, Kazuyuki; Suzuki, Kengo; Suzuki, Shunya; Tohmiya, Hiraku; Hashimoto, Kimiko; Nakata, Masaya

doi:10.1016/j.tetlet.2006.12.121

Cited by 26 publications

(16 citation statements)

References 39 publications

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“…[114] This thiopeptide is very closely related to thiostrepton, only differing in the dehydroalanine-valine fragment attached to the 7-position of the dihydroquinoline instead of an alanine-isoleucine residue. The overall strategy used by Hashimoto, Nakata, and co-workers is similar to the route used by Nicolaou et al to thiostrepton in terms of the disconnections of the major building blocks, although they elected to form the right-side dihydroquinoline-containing macrocycle first.…”

Section: Siomycin Amentioning

confidence: 98%

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

2007

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Amino acids, the building blocks of proteins, also serve as precursors to a wide range of other naturally occurring substances including alkaloids, antibiotics, and, the subject of this Review, heterocyclic peptides. Simple alpha-amino acids are converted into complex arrays of heteroaromatic rings that display interesting and potent biological activity. The thiopeptide antibiotics, with their complex molecular architectures, are wonderful examples. In this Review we show how organic chemists have developed innovative methods for the synthesis of the heterocyclic ring systems, including routes inspired by the likely biosynthetic processes, and successfully assembled such building blocks into the final target molecule by application of orthogonal protecting groups and coupling methodologies.

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Section: Siomycin Amentioning

confidence: 98%

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

2007

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“…This group of peptides is divided into five classes (a–e) on the basis of the oxidation state of this nitrogen‐containing ring. This six‐membered ring is completely reduced to piperidine in the case of class a, whereas it is oxidized to form one double bond in the case of class b, resulting in the formation of a 1,2‐dehydropiperidine ring. It is a three double‐bond pyridine ring in the case of class d; and a hydroxypyridine in class e .…”

Section: Bacterial Antimicrobial Cyclopeptidesmentioning

confidence: 99%

Bacteria Hunt Bacteria through an Intriguing Cyclic Peptide

et al. 2018

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In the last few decades, peptides have been victorious over small molecules as therapeutics due to their broad range of applications, high biological activity, and high specificity. However, the main challenges to overcome if peptides are to become effective drugs is their low oral bioavailability and instability under physiological conditions. Cyclic peptides play a vital role in this context because they show higher stability under physiological conditions, higher membrane permeability, and greater oral bioavailability than that of their corresponding linear analogues. In this regard, cyclic antimicrobial peptides (AMPs) have gained considerable attention in the field of novel antibiotic development. Bacterial strains produce cyclic AMPs through two pathways: ribosomal and nonribosomal. This review provides an overview of the chemical classification of cyclic AMPs isolated from bacteria, and provides a description of their biological activity and mode of action.

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“…Proving itself to be highly rewarding in terms of synthetic strategies and tactics, the thiostrepton campaign also served as a prelude to the total synthesis of other members of the thiopeptide class of antibiotics, such as siomycin 177 and antibiotics GE2270A, 178,179 GE2270T 178 and GE 2270C, 178 as well as amythiamicins A-C. 180 Amythiamicin D was first synthesized in 2004 by the Moody group. 181 …”

Section: Highlights Of Contributions From the Author’s Laboratoriesmentioning

confidence: 99%

Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance

et al. 2012

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The advent of organic synthesis and the understanding of the molecule as they occurred in the nineteenth century and were refined in the twentieth century constitute two of the most profound scientific developments of all time. These discoveries set in motion a revolution that shaped the landscape of the molecular sciences and changed the world. Organic synthesis played a major role in this revolution through its ability to construct the molecules of the living world and others like them whose primary element is carbon. Although the early beginnings of organic synthesis came about serendipitously, organic chemists quickly recognized its potential and moved decisively to advance and exploit it in myriad ways for the benefit of mankind. Indeed, from the early days of the synthesis of urea and the construction of the first carbon-carbon bond, the art of organic synthesis improved to impressively high levels of sophistication. Through its practice, today chemists can synthesize organic molecules—natural and designed—of all types of structural motifs and for all intents and purposes. The endeavor of constructing natural products—the organic molecules of nature—is justly called both a creative art and an exact science. Often called simply total synthesis, the replication of nature’s molecules in the laboratory reflects and symbolizes the state of the art of synthesis in general. In the last few decades a surge in total synthesis endeavors around the world led to a remarkable collection of achievements that covers a wide ranging landscape of molecular complexity and diversity. In this article, we present highlights of some of our contributions in the field of total synthesis of natural products of biological and medicinal importance. For perspective, we also provide a listing of selected examples of additional natural products synthesized in other laboratories around the world over the last few years.

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Total synthesis of siomycin A

Cited by 26 publications

References 39 publications

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

Bacteria Hunt Bacteria through an Intriguing Cyclic Peptide

Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance

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