Prodigiosin synthesis in Serratia marcescens: isolation of a pyrrole-containing precursor

Santer, Ursula V.; Vogel, Henry J.

doi:10.1016/0006-3002(56)90500-5

Cited by 43 publications

(25 citation statements)

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“…1. A, Pyrryldipyrrylmethene structure of prodigiosin confirmed by synthesis (RApOPORT and HOLDEN, 1960, 1962); B, original tripyrrylmethene structure proposed by Paramount to final elucidation of the structure was identification of a compound excreted by mutant 9-3-3 of S. marcescens and shown to be a precursor of prodigiosin (SANTER and VOGEL, 1956). WASSERMAN et al (1960b) concluded that the compound was a 2,2'-bipyrrole aldehyde with the probable structure of 4-methoxy-2,2' -bipyrrole-5-carboxaldehyde (MBC) ; this compound could condense with 2-methyl-3-amylpyrrole (MAP) to form prodigiosin, making the pigment a pyrryldipyrrylmethene (see Fig.…”

Section: O-ocmentioning

confidence: 91%

“…RIZKI (1954 b) identified syntrophic pigment as prodigiosin by comparison of ultraviolet and visible absorption spectra. SANTER and VOGEL (1956) demonstrated by chromatography and the visible absorption spectrum that prodigiosin was formed when mutant W-1 was provided with the crystalline intermediate accumulated by 9-3-3. The pigment formed by the interaction of orange (OF) and white (WF) mutants was also established as prodigiosin by chromatography and by ultraviolet and visible spectra (GREEN and WILLIAMS, 1957). The most definitive analyses of syntrophic interactions and demonstration that the pigments formed were indeed prodigiosin were recently completed by WILLIAMS (1965).…”

Section: Biosynthesismentioning

confidence: 96%

“…This mutant does not form the volatile precursor MAP, but accumulates MBC, the stable precursor (SANTER and VOGEL, 1956), that provided the key to the structure of prodigiosin (WASSERMAN et al, 1960b;HOLDEN, 1960, 1962). If provided with MAP produced by mutants blocked at points 1, 2, 3 or 4, mutant 9-3-3 forms prodigiosin.…”

Section: Biosynthesismentioning

confidence: 97%

“…Several investigations established that pigmentation occurred because nonpigmented precursors produced by certain mutants diffused through the medium and were utilized for formation of pigment by other mutants. This phenomenon was called chromogenic induction by RIZKI (1954a), syntrophic pigmentation by WILLIAMS and GREEN (1956) and cross-feeding by SANTER and VOGEL (1956).…”

Section: Biosynthesismentioning

confidence: 97%

“…Biosynthetic studies by WAS-SERMAN, McKEON and SANTER (1960) established that MBC produced by mutant 9-3-3 did condense with synthetic MAP to form prodigiosin. The final step in establishing the structure of prodigiosin was taken when HOLDEN (1960,1962) synthesized MBC and found their synthetic compound to be identical to the precursor of SANTER and VOGEL (1956). Condensation of synthetic MBC and MAP under acidic conditions gave a compound identical to natural prodigiosin.…”

Section: O-ocmentioning

confidence: 99%

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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: O-ocmentioning

confidence: 91%

Section: Biosynthesismentioning

confidence: 96%

Section: Biosynthesismentioning

confidence: 97%

Section: Biosynthesismentioning

confidence: 97%

Section: O-ocmentioning

confidence: 99%

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Biosynthesis

1967

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The Total Synthesis of Pyrrole Pigments

Jackson¹

1973

Total Synthesis of Natural Products

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Purification and Kinetic Characterization of the Essential Condensation Enzymes Involved in Prodiginine and Tambjamine Biosynthesis

et al. 2019

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Prodiginines and tambjamines are related families of bioactive alkaloid natural products with pharmaceutical potential. Both compound families result from a convergent biosynthetic pathway ending in the condensation of a conserved bipyrrole core with a variable partner. This reaction is performed by unique condensation enzymes, and has the potential to be manipulated to produce new pyrrolic compounds. We have purified and reconstituted the in vitro activity of the condensation enzymes PigC and TamQ from Pseudoalteromonas sp., which are involved, respectively, in the prodiginine and tambjamine biosynthetic pathways. Kinetic analysis confirmed a Uni Uni Bi Uni ping‐pong reaction sequence with competitive and uncompetitive substrate inhibition for PigC and TamQ respectively. The kinetic parameters of each enzyme provide insight into their differing substrate scope, and suggest that TamQ may have evolved a wide substrate tolerance that can be used for the production of novel prodiginines and tambjamines.

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Prodigiosin synthesis in Serratia marcescens: isolation of a pyrrole-containing precursor

Cited by 43 publications

References 5 publications

Biosynthesis

Biosynthesis

The Total Synthesis of Pyrrole Pigments

Purification and Kinetic Characterization of the Essential Condensation Enzymes Involved in Prodiginine and Tambjamine Biosynthesis

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