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Ag, Kozlovskiĭ; Vm, Adanin; Hm, Dahse; Gräfe, U.

doi:10.1023/a:1010225017054

Cited by 17 publications

(10 citation statements)

References 4 publications

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“…5-N-acetylardeemin, 2 aszonalenin and epiaszonalenin as well as their acetylated form 1,3,4 belong to the first subgroup. Examples of b-configured derivatives are roquefortines C and D, 5-7 fructigenines A and B (verrucofortine), 8,9 rugulosuvines A and B, 10 brevicompanines A, B and C, 11, 12 as well as amauromine. 13 Both a-and b-configured C3-dimethylallyl residues are found in the structure of epiamauromine derived from two tryptophan molecules.…”

Section: Introductionmentioning

confidence: 99%

Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT

Yin

Xie

et al. 2010

Org. Biomol. Chem.

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Six beta-configured reversely C3-prenylated pyrrolo[2,3-b]indoles were successfully prepared by using a recombinant prenyltransferase from Neosartorya fischeri. For this purpose, the putative prenyltransferase gene NFIA_074280 (termed herewith cdpC3PT) was cloned into pQE60 and overexpressed in Escherichia coli. The overproduced His(6)-CdpC3PT was purified to near homogeneity and incubated with five cyclic tryptophan-containing dipeptides in the presence of dimethylallyl diphosphate (DMAPP). All of the substrates were accepted by CdpC3PT and converted to reversely C3-prenylated pyrrolo[2,3-b]indoles. Using cyclo-l-Trp-l-Trp as substrate, both mono- and diprenylated derivatives were obtained. The structures of the enzymatic products were confirmed by HR-ESI-MS, (1)H- and (13)C-NMR analyses as well as by long-range (1)H-(13)C connectivities in heteronuclear multiple-bond correlation (HMBC) spectra after preparative isolation. (1)H-(1)H spatial correlations in nuclear overhauser effect spectroscopy (NOESY) were used for determination of absolute configuration. The K(M) values were determined at about 1.5 mM for DMAPP and in the range from 0.22 to 5.5 mM for cyclic dipeptides. The turnover number k(cat) were found in the range of 0.023 to 0.098 s(-1) and specificity constants k(cat)/K(M) from 14.2 to 122.7 M(-1) s(-1). In contrast to the products of AnaPT bearing alpha-configured C3-dimethylallyl residues, the C3-prenyl moieties in the products of CdpC3PT have a beta-configuration. Discovery and characterisation of CdpC3PT expand the usage of the chemoenzymatic approach for stereospecific synthesis of C3-prenylated derivatives.

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Section: Introductionmentioning

confidence: 99%

Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT

Yin

Xie

et al. 2010

Org. Biomol. Chem.

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“…1) from P. rugulosum and P. piscarium had moderate cytotoxicity against L-929, K562 and Hela cells. 13 Amauromine (Fig. 1) from Amauroascus sp.…”

Section: Introductionmentioning

confidence: 99%

Reconstruction of pyrrolo[2,3-b]indoles carrying an α-configured reverse C3-dimethylallyl moiety by using recombinant enzymes

et al. 2010

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Nine reversely C3-prenylated pyrrolo[2,3-b]indoles were successfully prepared by using two recombinant enzymes involved in the biosynthesis of acetylaszonalenin from Neosartorya fischeri. The prenyltransferase AnaPT catalysed the conversion of six tryptophan-containing cyclic dipeptides to reversely C3-prenylated indoline derivatives. Using cyclo-L-Trp-L-Trp as substrate, both mono- and diprenylated indolines were obtained. Two of the AnaPT products were acetylated at position N1 by the acetyltransferase AnaAT. The structures of the obtained compounds were characterised by HR-ESI-MS, (1)H- and (13)C-NMR analyses as well as by long-range (1)H-(13)C connectivities in heteronuclear multiple-bond correlation (HMBC) spectra after preparative isolation. Their absolute configurations were determined by analysing the (1)H-(1)H spatial correlations in rotating-frame nuclear overhauser effect spectroscopy (ROESY).

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“…Penicillium species are known to produce numerous alkaloids, in which some diketopiperazine-type alkaloids have been reported so far. [1][2][3][4][5] In the course of our on-going research on the secondary metabolites of marinederived fungi, we have investigated the chemistry of the methylethylketone extract of the Penicillium sp. JF-72, and the study resulted in the isolation of three indole-containing diketopiperazine alkaloids (1)(2)(3), including a new natural compound (2) and a new metabolite (3).…”

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confidence: 99%

“…The absolute configuration of compound 2 was determined based on the biogenetic considerations of diketopiperazine alkaloids isolated from the fungal genus Penecillium, [1][2][3][4][5] and NOESY correlation between H-11 and H-17. In addition, comparison of its optical rotation value, + 140 (c 0.04, CHCl 3 ) with the reported compound was in good agreement with this assignment.…”

mentioning

confidence: 99%

“…As all the diketopiperazine alkaloids isolated from the fungi Penecillium showed the configuration at C-11 to be S, therefore the orientation of proton at C-11 of 3 could be assumed as α based on the biogenetic considerations. [1][2][3][4][5] In the NOESY spectrum, an NOE correlation observed between H-11 and H-16 indicated that the hydroxyl group at C-16 is β-oriented (Figure 2). Furthermore, H-11 and H-16 did not give any NOE correlation with the methoxy group, suggesting that the orientation of the methoxy group at C-17 is β, which is opposite to that of the methoxy group of verpacamide D. 8 The observation of unusual upfield-shifted proton chemical shift of the methoxy group could be rationalized by the presence of coplanar C-18 carbonyl group.…”

mentioning

confidence: 99%

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New Deoxyisoaustamide Derivative from the Marine-derived Fungus Penicillium sp. JF-72

Quang¹,

Lee²,

Sohn³

et al. 2013

Bulletin of the Korean Chemical Society

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Untitled

Cited by 17 publications

References 4 publications

Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT

Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT

Reconstruction of pyrrolo[2,3-b]indoles carrying an α-configured reverse C3-dimethylallyl moiety by using recombinant enzymes

New Deoxyisoaustamide Derivative from the Marine-derived Fungus Penicillium sp. JF-72

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