Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Hibino, Satoshi; Choshi, Tominari

doi:10.1039/b007740m

Cited by 143 publications

(44 citation statements)

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“…Prenylated indole derivatives are a large class of alkaloids containing a tryptophan moiety substituted with isoprenic moieties, and are mostly found in fungi of the genera Aspergillus and Penicillium (Hibino & Choshi, 2001;Lounasmaa & Tolvanen, 2000;Williams et al, 2000). Most of these alkaloids contain a second amino acid, forming cyclic dipeptides with a diketopiperazine structure.…”

Section: Introductionmentioning

confidence: 99%

“…Interestingly, DMATS, CloQ and LtxC share no sequence similarity, despite their similar biochemical properties. In order to obtain more insight into the mechanism and evolution of this class of prenyltransferases, we were interested to identify additional members of this class.Prenylated indole derivatives are a large class of alkaloids containing a tryptophan moiety substituted with isoprenic moieties, and are mostly found in fungi of the genera Aspergillus and Penicillium (Hibino & Choshi, 2001;Lounasmaa & Tolvanen, 2000;Williams et al, 2000). Most of these alkaloids contain a second amino acid, forming cyclic dipeptides with a diketopiperazine structure.…”

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Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus

2005

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A putative prenyltransferase gene, ftmPT1, was identified in the genome sequence of Aspergillus fumigatus. ftmPT1 was cloned and expressed in Escherichia coli, and the protein FtmPT1 was purified to near homogeneity and characterized biochemically. This enzyme was found to catalyse the prenylation of cyclo-L-Trp-L-Pro (brevianamide F) at the C-2 position of the indole nucleus. FtmPT1 is a soluble monomeric protein, which does not contain the usual prenyl diphosphate binding site (N/D)DXXD found in most prenyltransferases, and which does not require divalent metal ions for its enzymic activity. K m values for brevianamide F and dimethylallyl diphosphate were determined as 55 and 74 mM, respectively. The turnover number was 5?57 s "1 . FtmPT1 showed a high substrate specificity towards dimethylallyl diphosphate, but accepted different tryptophan-containing cyclic dipeptides. Together with dimethylallyltryptophan synthase of ergot alkaloid biosynthesis, FtmPT1 belongs to a new group of prenyltransferases with aromatic substrates. INTRODUCTIONTrans-prenyltransferases (Bohlmann et al., 1998;Liang et al., 2002;Sacchettini & Poulter, 1997) are involved in the biosynthesis of terpenoids from C-5 units. These enzymes usually contain one or more prenyl diphosphate binding motifs, (N/D)DXXD, in their sequences (Bohlmann et al., 1998;Liang et al., 2002;Sacchettini & Poulter, 1997). Their enzymic reaction depends strictly on the presence of metal ions such as Mg 2+ or Mn 2+ (Bohlmann et al., 1998;Liang et al., 2002). A special group of prenyltransferases catalyses the attachment of a prenyl moiety to an aromatic nucleus. These enzymes show similar sequence motifs and metal ion requirements to those of the trans-prenyltransferases. Examples of this group are the prenyltransferases involved in the biosynthesis of the primary metabolites ubiquinone (Turunen et al., 2004), menaquinone (Suvarna et al., 1998), tocopherol (Schledz et al., 2001) and plastoquinone (Collakova & DellaPenna, 2001), and the prenyltransferase involved in the formation of the plant secondary metabolite shikonin (Yazaki et al., 2002). All these enzymes are membrane-bound proteins.In contrast, the dimethylallyltryptophan synthase (DMATS) that catalyses the prenylation of tryptophan at position C-4 of the indole nucleus during ergot alkaloid biosynthesis in the fungus Claviceps has been found to be a soluble protein and is active in a metal-free buffer containing EDTA (Cress et al., 1981;Lee et al., 1976;Tsai et al., 1995; Tudzynski et al., 1999). Recently, two further soluble prenyltransferases with aromatic substrates, which are active in the absence of metal ions and contain no (N/D)DXXD motifs, CloQ involved in the biosynthesis of clorobiocin from Streptomyces roseochromogenes (Pojer et al., 2003) and LtxC involved in the biosynthesis of lyngbyatoxins from Lyngbya majuscula (Edwards & Gerwick 2004), have been identified. Very recently, we identified an orthologue of DMATS, FgaPT2, in the genome sequence of Aspergillus fumigatus (Unsöld & Li, 2005). Inte...

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus

2005

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“…[2] Among these,t he enantioselective MBH reaction of isatins wasp articularly attractives incet he MBH adducts, [3] 3-substituted 3-hydroxy-2-oxindoles, constitute the core building blocks of many valuable drug candidates. [4][5] In 2010, Zhou and coworkers reported the first MBH reactiono fi satin with acrolein catalyzed by ß-isocupreidine 1a (ß-ICD) providing the oxindole derivatives in excellent enantioselectivity ( Figure 1). [6] Shi et al reported the ß-ICD-catalyzed asymmetric MBH reactiono f1 -naphthyl acrylate with isatinst og enerate the oxindoles in good ee values (up to 94 %).…”

Section: Introductionmentioning

confidence: 99%

Tunable Bifunctional Phosphine–Squaramide Promoted Morita–Baylis–Hillman Reaction of N‐Alkyl Isatins with Acrylates

et al. 2015

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As erieso fh ighly tunable bifunctional phosphine-squaramide H-bond donor organocatalysts 6 has been synthesizedf rom inexpensivea nd commercially available b-amino alcohols in moderate yields.C atalyst 6f can efficiently promote the asymmetric Morita-Baylis-Hillman (MBH) reaction of N-alkyl isatins with acrylate estersp roviding the chiral 3-substituted 3-hydroxy-2-oxindoles in good yields and enantioselectivities( up to 93 % yield and9 5% ee), in which the challenging substrate tert-butyl acrylate 9d,p rovided the best ee value to date.M oreover, this methodology was applied successfully in the synthesis of chiral cyclic spiropyrrolizidineoxindolea nd g-butyrolactone derivatives without enantioselectivity deterioration. Thep ossible mechanism of this MBH reactionw as also investigated by 31 PNMR, ESI-MS and KIE studies.T he KIE experiments show that the electrophilic addition of N-methyl isatin to the complexo f acrylate ester and phophine-squaramide is the ratedeterming step of the asymmetric MBH reaction.

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“…Numerous indoles occur in many active medicine compounds for human health [1,2]. In particular, bis(indolyl)methanes possess a wide range of pharmaceutical activities, such as serving as anti-bacterial and anti-fungal agents [3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes

Ren

Wang

2017

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An efficient procedure has been researched for the solvent-free synthesis of bis(indolyl)methanes via a one-pot reaction of indoles and aldehydes or ketones promoted by PEG 1000 -based dicationic acidic ionic liquid (PEG 1000 -DAIL). The catalyst PEG 1000 -DAIL could be reused seven times with excellent results. Furthermore, through this method, a highly chemoselective reaction of benzaldehyde and acetophenone with indole could be achieved.

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Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Cited by 143 publications

References 115 publications

Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus

Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus

Tunable Bifunctional Phosphine–Squaramide Promoted Morita–Baylis–Hillman Reaction of N‐Alkyl Isatins with Acrylates

PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes

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