Studies related to the biosynthesis of prodigiosin in Serratiamarcescens

Wasserman, Harry H.; McKeon, James E.; Santer, Ursula V.

doi:10.1016/0006-291x(60)90211-4

Cited by 44 publications

(19 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This enzyme catalyses the decarboxylative condensation of l ‐alanine with pimeloyl CoA as part of biotin biosynthesis (Webster et al ., 2000). As it has been shown previously that serine is incorporated into the section of prodigiosin that derives from MBC (Wasserman et al ., 1960; Harris et al ., 2004), we propose that the C‐terminal domain of PigH performs a similar condensation of serine with the pyrrolyl‐β‐ketothioester unit, releasing it from its ACP. The resulting amino diketone would then cyclize, dehydrate and tautomerize (possibly spontaneously) to give HBM.…”

Section: Discussionmentioning

confidence: 84%

Biosynthesis of the red antibiotic, prodigiosin, in Serratia: identification of a novel 2‐methyl‐3‐n‐amyl‐pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces

Williamson

Simonsen

Ahmed

et al. 2005

Molecular Microbiology

206

241

View full text Add to dashboard Cite

SummaryThe biosynthetic pathway of the red-pigmented antibiotic, prodigiosin, produced by Serratia sp. is known to involve separate pathways for the production of the monopyrrole, 2-methyl-3-n-amyl-pyrrole (MAP) and the bipyrrole, 4-methoxy-2,2 ¢ -bipyrrole-5-carbaldehyde (MBC) which are then coupled in the final condensation step. We have previously reported the cloning, sequencing and heterologous expression of the pig cluster responsible for prodigiosin biosynthesis in two Serratia sp. In this article we report the creation of in-frame deletions or insertions in every biosynthetic gene in the cluster from Serratia sp. ATCC 39006. The biosynthetic intermediates accumulating in each mutant have been analysed by LC-MS, cross-feeding and genetic complementation studies. Based on these results we assign specific roles in the biosynthesis of MBC to the following Pig proteins: PigI, PigG, PigA, PigJ, PigH, PigM, PigF and PigN. We report a novel pathway for the biosynthesis of MAP, involving PigD, PigE and PigB. We also report a new chemical synthesis of MAP and one of its precursors, 3-acetyloctanal. Finally, we identify the condensing enzyme as PigC. We reassess the existing literature and discuss the significance of the results for the biosynthesis of undecylprodigiosin by the Red cluster in Streptomyces coelicolor A3(2).

show abstract

Section: Discussionmentioning

confidence: 84%

Biosynthesis of the red antibiotic, prodigiosin, in Serratia: identification of a novel 2‐methyl‐3‐n‐amyl‐pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces

Williamson

Simonsen

Ahmed

et al. 2005

Molecular Microbiology

206

241

View full text Add to dashboard Cite

show abstract

“…In 1956, Santer and Vogel 41 isolated 4-methoxy-2,2′-bipyrrole-5-carboxaldehyde (MBC, 6 ) from an S. marcescens mutant (9-3-3) blocked in prodigiosin biosynthesis and demonstrated that it could be converted to prodigiosin by a second strain also blocked in prodigiosin production. In 1960, Wasserman et al 124 found that exposure of S. marcescens strain 9-3-3 to vapors of synthetic methylamylpyrrole (MAP, 7 ) resulted in the formation of prodigiosin within a few minutes. Evidence that the condensation of 6 and 7 (Figure 31) is enzyme-catalyzed was reported by Williams et al in 1965, 125 who found that the condensation of MBC and MAP by a cell lysate of strain 9-3-3 is significantly less efficient at slightly elevated temperatures (>35 °C).…”

Section: Biosynthesismentioning

confidence: 99%

Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products

et al. 2016

View full text Add to dashboard Cite

The prodiginine family of bacterial alkaloids is a diverse set of heterocyclic natural products that have likely been known to man since antiquity. In more recent times, these alkaloids have been discovered to span a wide range of chemical structures that possess a number of interesting biological activities. This review provides a comprehensive overview of research undertaken toward the isolation and structural elucidation of the prodiginine family of natural products. Additionally, research toward chemical synthesis of the prodiginine alkaloids over the last several decades is extensively reviewed. Finally, the current, evidence-based understanding of the various biosynthetic pathways employed by bacteria to produce prodiginine alkaloids is summarized.

show abstract

“…Proc., p. 354, 1963). All of these strains produce the immediate monopyrrole precursor of prodigiosin, 2-methyl-3-amylpyrrole, since they are both donors and acceptors to MBC-producing mutant 933 (19). Mutant H-462 was of great interest to us as a source of a precursor of HBC in the bipyrrole pathway, but our attempts to isolate such a precursor have been unsuccessful.…”

Section: Resultsmentioning

confidence: 99%

Separation of Prodigiosenes and Identification as Prodigiosin Syntrophic Pigment from Mutant Pairs of Serratia marcescens1

Hearn¹,

Williams²,

Burgus³

et al. 1972

Applied Microbiology

View full text Add to dashboard Cite

Countercurrent distribution is capable of resolving mixtures of closely related prodigiosene pigments. Syntrophic pigment produced by several pairs of Serratia marcescens color mutants was identified as prodigiosin (2-methyl-3amyl-6-methoxyprodigiosene) by countercurrent distribution, soda lime pyrolysis, and other techniques. The metabolic block of mutant strain H-462, derived from parent strain HY, was located between the blocks of mutant strains OF and WF, both derived from parent strain Nima.

show abstract

Studies related to the biosynthesis of prodigiosin in Serratiamarcescens

Cited by 44 publications

References 6 publications

Biosynthesis of the red antibiotic, prodigiosin, in Serratia: identification of a novel 2‐methyl‐3‐n‐amyl‐pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces

Biosynthesis of the red antibiotic, prodigiosin, in Serratia: identification of a novel 2‐methyl‐3‐n‐amyl‐pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces

Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products

Separation of Prodigiosenes and Identification as Prodigiosin Syntrophic Pigment from Mutant Pairs of Serratia marcescens1

Contact Info

Product

Resources

About