Total synthesis of pyrrolnitrin, a new antibiotic.

Nakano, Hirofumi; Umio, Suminori; Kariyone, Kazuo; Tanaka, Kuniyoshi; Kishimoto, Takao; Noguchi, Hideyo; Ueda, I.; Nakamura, Hitoshi; Morimoto, Toshiharu

doi:10.1016/s0040-4039(00)90255-7

Cited by 51 publications

(31 citation statements)

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“…Chemical degradation of the molecule by IMANAKA et al (1965 a) established the structure as 3-chloro-4-(2' -nitro-3'-chlorophenyl)-pyrrole (I); this structure was confirmed by synthesis in the Research Laboratories of Fujisawa Pharmaceutical Co., Ltd., Osaka, Japan (NAKANO et al, 1966).…”

Section: Lincomycinmentioning

confidence: 95%

Biosynthesis

1967

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All rights, especially that of translation into f oreign 1anguages, reserved. It is also forbidden to reproduce this book, either who1e or in part, by photomechanical means (photostat, microfilm and/or microcard) or by other procedure without written pennission from Springcr-Vcrlag Berlin Heide1bCig GmbH. DedicationFor most areas of scientific pursuit, there is usually that rare investigator who has the imagination to conceive ideas, who has faith in his visions, and who has the ability to critically test his concepts in the laboratory. Almost invariably, this scientist also inspires younger men to enthusiastically enter into his research program. To him should go the accolades and the recognitions of the esteem in which he is held. As only a small part of this esteem, we wish to dedicate these books to Professor SELMAN A. W AKSMAN in appreciation of his leadership and contributions in all facets of antibiotic research. PrefaceThe idea for publishing these books on the mechanism of action and on the biosynthesis of antibiotics was born of frustration in our attempts to keep abreast of the literature. Gone were the years when we were able to keep a bibliography on antibiotics and feel confident that we could find everything that was being published on this sUbject. These fields of investigation were moving forward so rapidly and were encompassing so wide a range of specialized areas in microbiology and chemistry that it was almost impossible to keep abreast of developments. In our naivete and enthusiasm, however, we were unaware that we were toying with an idea that might enmesh us, that we were creating an entity with a life of its own, that we were letting loose a Golom who instead of being our servant would be our master.That we set up ideals for these books is obvious; they would be current guides to developments and information in the areas of mechanism of action and biosynthesis of antibiotics. For almost every subject, we wished to enlist the aid of an investigator who himself had played a part in determining the nature of the phenomena that were being discussed. One concept for the books was that they include only antibiotics for which a definitive, well-documented mechanism of action or biosynthetic pathway was known. Yet, such an approach would not entirely serve the purpose we projected, for it would not encompass all of the information available in these fields of antibiotic investigations and blind searches for the original literature would still have to be made. We therefore chose to include any and all antibiotics about which some pertinent information had been published. It was obvious even at the start that such a compilation, integration, and analysis of information could never be complete unless scientific investigations ceased at the moment the last manuscript was submitted-an end that was neither desirable nor possible. An addendum was therefore included at the end of the volume and left open for the addition of new information until the last pages of the regular articles had been printed.The...

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Section: Lincomycinmentioning

confidence: 95%

Biosynthesis

1967

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“…PRN, isolated from Pseudomonas pyrrocinia and various other pseudomonads, was classified as halometabolite in as early as 1964 [38]. Later, the compound was biosynthesized using tryptophan as supplement in the medium [53] and chemically synthesized by Nakano et al [54]. Biosynthesis of PRN in Pseudomonas aureofaciens ATCC 15926 has shown that L-tryptophan is a direct precursor (Figure 1) [53].…”

Section: Pyrrolnitrin (Prn)mentioning

confidence: 99%

“…Modern synthetic targets for chemical synthesis require regiospecific polysubstituted aromatic or heteroaromatic components [60]. PRN is chemically synthesized by α-block of pyrrole ring and 2-nitro-3-chloroacetophenone, and subsequent chlorination at 4-position and oxidation of methyles using sulfurilchloride followed by decarboxylation [54]. In another approach, 2-Methyl-4-(2-nitro-3-chloro-phenyl)-5-ethoxycarbonyl-pyrrole was prepared in various steps from 2-amino-3-chloro-toluene [61].…”

Section: Pyrrolnitrin (Prn)mentioning

confidence: 99%

Microbial Pyrrolnitrin: Natural Metabolite with Immense Practical Utility

et al. 2019

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Pyrrolnitrin (PRN) is a microbial pyrrole halometabolite of immense antimicrobial significance for agricultural, pharmaceutical and industrial implications. The compound and its derivatives have been isolated from rhizospheric fluorescent or non-fluorescent pseudomonads, Serratia and Burkholderia. They are known to confer biological control against a wide range of phytopathogenic fungi, and thus offer strong plant protection prospects against soil and seed-borne phytopathogenic diseases. Although chemical synthesis of PRN has been obtained using different steps, microbial production is still the most useful option for producing this metabolite. In many of the plant-associated isolates of Serratia and Burkholderia, production of PRN is dependent on the quorum-sensing regulation that usually involves N-acylhomoserine lactone (AHL) autoinducer signals. When applied on the organisms as antimicrobial agent, the molecule impedes synthesis of key biomolecules (DNA, RNA and protein), uncouples with oxidative phosphorylation, inhibits mitotic division and hampers several biological mechanisms. With its potential broad-spectrum activities, low phototoxicity, non-toxic nature and specificity for impacts on non-target organisms, the metabolite has emerged as a lead molecule of industrial importance, which has led to developing cost-effective methods for the biosynthesis of PRN using microbial fermentation. Quantum of work narrating focused research efforts in the emergence of this potential microbial metabolite is summarized here to present a consolidated, sequential and updated insight into the chemistry, biology and applicability of this natural molecule.

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“…Additionally, there are a number of pyrrole-containing small molecules that exhibit useful biological activities [1][2][3][4][5][6][7]. A lot of effort has been spent on developing practical methods for the synthesis of pyrrole units that incorporate appropriate functionality [8,9].…”

Section: Introductionmentioning

confidence: 99%