Utilization of13C-13C coupling in structural and biosynthetic studies. VII1) the structure and biosynthesis of vulgamycin.

Seto, Haruo; Sato, Tsutomu; Urano, Shiro; Uzawa, Jun; Yonehara, Hiroshi

doi:10.1016/0040-4039(76)80117-7

Cited by 59 publications

(47 citation statements)

References 7 publications

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“…The predominant metabolite is the branched octaketide enterocin (Sitachitta et al 1996). This metabolite, also called vulgamycin, was originally isolated in 1976 from edaphic streptomycetes by two Japanese groups Seto et al 1976;Tokuma et al 1976) and more recently from a marine tunicate from Australia (Kang et al 1996). Structurally related compounds also identified in 'S.…”

Section: Biosynthesis and Engineering Of Enterocin-wailupemycin Analomentioning

confidence: 97%

Exploiting marine actinomycete biosynthetic pathways for drug discovery

Moore

Kalaitzis

Xiang

2005

Antonie Van Leeuwenhoek

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Drug discovery relies on the generation of large numbers of structurally diverse compounds from which a potential candidate can be identified. To this end, actinomycetes have often been exploited because of their ability to biosynthesize an impressive array of novel metabolites particularly polyketides. The genetic organization of polyketide synthases (PKSs) makes them readily amenable to manipulation, and thus re-engineering artificial or hybrid PKSs to produce unnatural natural products is a reality. This review highlights two approaches we have used to generate novel polyketides by manipulating genes responsible for starter unit biosynthesis in the 'Streptomyces maritimus' enterocin type II PKS. Our preliminary investigation into the biosynthesis of neomarinone, a rare marine actinomycete-derived meroterpenoid, is also presented.

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Section: Biosynthesis and Engineering Of Enterocin-wailupemycin Analomentioning

confidence: 97%

Exploiting marine actinomycete biosynthetic pathways for drug discovery

Moore

Kalaitzis

Xiang

2005

Antonie Van Leeuwenhoek

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“…44 The enterocins and wailupemycins drew the interest of researchers in part because of their unique polyketide carbon skeletons, which labeling studies during the mid-1970s revealed were derived from an uncommon benzoate starter unit along with seven malonate extender units that underwent a Favorskii-like rearrangement to yield the observed range of carbon skeletons. 45 More than twenty years after labeling-based insights were obtained, the genetic basis for biosynthesis of these natural products was finally unveiled and revealed information unattainable through strictly chemical-based studies.…”

Section: 2000–2010: From the First Marine Natural Product Biosynthementioning

confidence: 99%

“…1) also afforded clues as to the molecular basis for the unusual Favorskii-like carbon skeleton rearrangement, 43 which labeling studies had suggested was key in yielding the diverse cyclization modes observed for these compounds. 45 From the gene cluster, a flavin-dependent oxygenase protein product, EncM, was identified as the prime candidate for catalyzing oxidative carbon-carbon bond rearrangements. 43 Later biochemical characterization of EncM confirmed its role in the observed Favorskii-type rearrangement, providing evidence that this remarkable enzyme was responsible for not only carbon bond rearrangement, but also played key roles in two aldol condensations and reactions forming two heterocycles within this group of marine metabolites (Fig.…”

Section: 2000–2010: From the First Marine Natural Product Biosynthementioning

confidence: 99%

A sea of biosynthesis: marine natural products meet the molecular age

2011

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The years 2000 through mid-2010 marked a transformational period in understanding of the biosynthesis of marine natural products. During this decade the field emerged from one largely dominated by chemical approaches to understanding biosynthetic pathways to one incorporating the full force of modern molecular biology and bioinformatics. Fusion of chemical and biological approaches yielded great advances in understanding the genetic and enzymatic basis for marine natural product biosynthesis. Progress was particularly pronounced for marine microbes, especially actinomycetes and cyanobacteria. During this single decade, both the first complete marine microbial natural product biosynthetic gene cluster sequence was released as well as the first entire genome sequence for a secondary metabolite-rich marine microbe. The decade also saw tremendous progress in recognizing the key role of marine microbial symbionts of invertebrates in natural product biosynthesis. Application of genetic and enzymatic knowledge led to genetic engineering of novel “unnatural” natural products during this time, as well as opportunities for discovery of novel natural products through genome mining. The current review highlights selected seminal studies from 2000 through to June 2010 that illustrate breakthroughs in understanding of marine natural product biosynthesis at the genetic, enzymatic, and small-molecule natural product levels. A total of 154 references are cited.

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“…Biosynthetically, enterocin (257) is derived from an unusual benzoate starter unit and seven malonate molecules which undergoes a rare Favorskii-like carbon rearrangement, followed by cyclization ( Figure 141) [390] . Several structural analogous of enterocin (257) were reviewed and characterized by their specific α-pyrone e.g.…”

Section: : R= Oh 258: R = H 259 260mentioning

confidence: 99%