The origin of naturally-occurring acetylenes

Bu’Lock, J. D.; Smith, G. N.

doi:10.1039/j39670000332

Cited by 38 publications

(25 citation statements)

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“…Two distinct proposals for the biogenesis of acetylenic bonds. A. Desaturation of existing alkene functionality through an iron-catalyzed dehydrogenation with molecular oxygen [26]. Electrons are provided by either NADH or NADPH.…”

Section: Future Directionsmentioning

confidence: 99%

“…[2][3][4][5][6][7][8][9][10][11][12][13][14] C]Malonate labels the even-numbered carbons in dehydromatricariol 3I, while C-9 and C-10 specifically originated from acetate [9]. [10-14 C]Oleate was transformed to linoleate, crepenynate, dehydrocrepenynate and 3I by the basidiomycete Melanoleuca (Tricoloma) grammopodicum [26]. In contrast to plants, it is relatively common to observe the accumulation of acetylenic fatty acids in fungi.…”

Section: 13mentioning

confidence: 99%

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Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

290

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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Section: Future Directionsmentioning

confidence: 99%

Section: 13mentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

290

228

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“…A detailed exposition of, and further support for the hypothesis that the natural polyacetylenes are derived from C 18 fatty acids, is presented by and Bu'LoCK and SMITH (1967). In this scheme, crepenynic acid (actadec 9-en-12-ynoic acid) is a key intermediate.…”

Section: Lincomycinmentioning

confidence: 96%

“…Only very small amounts of penicillin N and cephalosporin C are present in the mycelium of the Cephalosporium sp. and it appears that these antibiotics are either confined to a very small proportion of the total cell volume or are excreted by the cell against a concentration gradient (SMITH et al, 1967).Electrophoresis and chromatography on paper, followed by radioautography, has indicated that labelled deacetylcephalosporin C, as well as cephalosporin C itself and penicillin N, is present in the mycelium of the Cephalosporium sp. suspended in shake-flasks in the presence of L-valine-1-14 C. However, radioactivity appeared in cephalosporin C before it was detected in deacetylcephalosporin C. It is therefore likely that the latter is produced from the former by an acetyl esterase and is not an intermediate in the biosynthetic pathway.…”

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confidence: 96%

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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“…But preliminary biosynthetic studies by P. V. R. Shannon (reported by BEW, CHAPMAN, JONES, LOWE and LOWE, 1966) indicate that the diyne-allene system of marasin is formed by enzymic isomerisation of a conjugated triyne precursor, not from an interrupted triyne grouping. BEW et al (1966) point out that the association of all known fungal allenes with a diacetylene group is explained by the biogenetic scheme proposed by Bu'LoCK (1965).…”

Section: Mechanism Of Triple Bond Formationmentioning

confidence: 97%

Biogenesis and Biological Activity of Polyacetylenes

Anchel¹

1967

Biosynthesis

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The origin of naturally-occurring acetylenes

Cited by 38 publications

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Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis

Biogenesis and Biological Activity of Polyacetylenes

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