Concise Three-Component Synthesis of Defucogilvocarcin M

Takemura, Isao; Imura, Koreaki; Matsumoto, Takashi; Suzuki, Keisuke

doi:10.1021/ol049261u

Cited by 53 publications

(21 citation statements)

References 11 publications

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“…Also, the 13 C NMR data of defuco-GE widely matched those of the recently synthesized compound defuco-GM with the exception of the C8 side chain signals (Table 2). [28] The minor compound defuco-GM (Scheme 1) had a UV spectrum identical to that of defuco-GE, but a mass of 336 g mol −1 , 14 amu less than defuco-GE; this is consistent with a C8 methyl group instead of a C8 ethyl group side chain.…”

Section: Identification Of Secondary Metabolites Accumulated By the Mmentioning

confidence: 96%

Inactivation of gilGT, Encoding a C‐Glycosyltransferase, and gilOIII, Encoding a P450 Enzyme, Allows the Details of the Late Biosynthetic Pathway to Gilvocarcin V to be Delineated

et al. 2006

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Resequencing of the gilGT gene, which encodes a putative glycosyltransferase (GT) that is 495 amino acids (aa) long, from the Streptomyces griseoflavus Gc3592 gilvocarcin V (GV) gene cluster, revealed that the previously reported gilGT indeed contains two genes. These are the larger gilGT, which encodes the C-glycosyltransferase GilGT (379 aa), and the smaller gilV gene, which encodes an enzyme of unknown function (116 aa). The gene gilV is located immediately upstream of gilGT in the GV gene cluster. In-frame deletion of gilGT created a mutant that accumulated defucogilvocarcin E (defuco-GE). The result proves the function of GilGT as a Cglycosyltransferase. Deletion of gilOIII, which is located immediately downstream of gilGT, led to a mutant that accumulated gilvocarcin E (GE). This confirms that the corresponding P450 enzyme, GilOIII, is involved in the vinyl-group formation of GV. Cross-feeding experiments in which GE, defuco-GE, and defucogilvocarcin V (defuco-GV) were fed to an early blocked mutant of the GV biosynthetic pathway, showed that neither GE nor any of the defuco-compounds was an intermediate of the pathway.

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Section: Identification Of Secondary Metabolites Accumulated By the Mmentioning

confidence: 96%

Inactivation of gilGT, Encoding a C‐Glycosyltransferase, and gilOIII, Encoding a P450 Enzyme, Allows the Details of the Late Biosynthetic Pathway to Gilvocarcin V to be Delineated

et al. 2006

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“…In this context, we herein report a complete, one-pot, enzymatic total synthesis of defucogilvocarcin M( 1 ), a model compound that contains the unique chromophore common to all members of the gilvocarcin group of natural products. [10] The reconstitution of this pathway then enabled further investigation into the details of the oxidative rearrangement process of GV biosynthesis by systematic variation of the enzyme mixture used. For this approach we suggest the term “combinatorial biosynthetic enzymology”.…”

mentioning

confidence: 99%

Enzymatic Total Synthesis of Defucogilvocarcin M and Its Implications for Gilvocarcin Biosynthesis

et al. 2011

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“…With a nice access to such strained starting materials, the [2+2+2] approach was put into practice for constructing polycyclic structures, which proved to have wide scope in natural product synthesis, such as, defucogilvocarcin (Fig. 14)18a and ravidomycins 18b…”

Section: The Gilvocarcin–ravidomycin Class Antibioticsmentioning

confidence: 99%

Lessons from total synthesis of hybrid natural products

Suzuki

2010

The Chemical Record

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There are a vast number of interesting and useful compounds that are readily found in nature. Mother Nature has acquired ingenious ways of generating molecular diversity in living cells responsible for regulation of various biochemical events. This has inspired research into the synthesis of biologically active compounds for use as antibiotics or in cancer therapy, for example. This account provides an overview of the work performed in the total synthesis of hybrid natural products and the interesting synthetic mechanisms encountered along the way.

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Concise Three-Component Synthesis of Defucogilvocarcin M

Abstract: [reaction: see text] Concise synthesis of defucogilvocarcin M was achieved via the [2 + 2 + 2] approach to beta-phenylnaphthalene structure.

Cited by 53 publications

References 11 publications

Inactivation of gilGT, Encoding a C‐Glycosyltransferase, and gilOIII, Encoding a P450 Enzyme, Allows the Details of the Late Biosynthetic Pathway to Gilvocarcin V to be Delineated

Inactivation of gilGT, Encoding a C‐Glycosyltransferase, and gilOIII, Encoding a P450 Enzyme, Allows the Details of the Late Biosynthetic Pathway to Gilvocarcin V to be Delineated

Enzymatic Total Synthesis of Defucogilvocarcin M and Its Implications for Gilvocarcin Biosynthesis

Lessons from total synthesis of hybrid natural products

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