Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

Campo, Vanessa Leiria; Martins, Maristela B.; Silva, Carlos Henrique Tomich de Paula da; Carvalho, Ivone

doi:10.1016/j.tet.2009.04.069

Cited by 16 publications

(19 citation statements)

References 24 publications

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“…These analyses confirmed the presence of the gliotoxins 1–3 and 8 , as well as their dehydroderivatives 5–7 and 9 . 15c, 16 We further identified cyclo(L-Phe-L-Ser) ( 10 ), 17 not previously reported from A. fumigatus extracts nor other gliotoxin-producing fungi, as well as bis - N -norgliovictin ( 11 ), a known A. fumigatus metabolite 18 not previously associated with the gli cluster.…”

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confidence: 62%

Identification of Cryptic Products of the Gliotoxin Gene Cluster Using NMR-Based Comparative Metabolomics and a Model for Gliotoxin Biosynthesis

et al. 2011

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Gliotoxin (1), a major product of the gli non-ribosomal peptide synthetase (NRPS) gene cluster, is strongly associated with virulence of the opportunistic human pathogen Aspergillus fumigatus. Despite identification of the gli cluster, the pathway of gliotoxin biosynthesis has remained elusive, in part because few potential intermediates have been identified. In addition, previous studies suggest that knowledge of gli-dependent metabolites is incomplete. Here we use differential analysis by 2D NMR spectroscopy (DANS) of metabolite extracts derived from gli knock-out and wild-type (WT) strains to obtain a detailed inventory of gli-dependent metabolites. DANS-based comparison of the WT metabolome with that of ΔgliZ, a knock-out strain devoid of the gene encoding the transcriptional regulator of the gli cluster, revealed nine novel gliZ-dependent metabolites including unexpected structural motifs. Their identification provides insight into gliotoxin biosynthesis and may benefit studies of the role of the gli cluster in A. fumigatus virulence. Our study demonstrates the utility of DANS for correlating gene expression and metabolite biosynthesis in microorganisms.

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confidence: 62%

Identification of Cryptic Products of the Gliotoxin Gene Cluster Using NMR-Based Comparative Metabolomics and a Model for Gliotoxin Biosynthesis

et al. 2011

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“…Other recent topics reporting the importance of intramolecular CH/p hydrogen bonds include a peptide metal complex, 77 2,5-diketopiparazines, 78 and atrope isomers of 2-arylindoline. 79…”

Section: 13mentioning

confidence: 99%

The CH/π hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates

Nishio¹

2011

Phys. Chem. Chem. Phys.

785

442

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The CH/π hydrogen bond is an attractive molecular force occurring between a soft acid and a soft base. Contribution from the dispersion energy is important in typical cases where aliphatic or aromatic CH groups are involved. Coulombic energy is of minor importance as compared to the other weak hydrogen bonds. The hydrogen bond nature of this force, however, has been confirmed by AIM analyses. The dual characteristic of the CH/π hydrogen bond is the basis for ubiquitous existence of this force in various fields of chemistry. A salient feature is that the CH/π hydrogen bond works cooperatively. Another significant point is that it works in nonpolar as well as polar, protic solvents such as water. The interaction energy depends on the nature of the molecular fragments, CH as well as π-groups: the stronger the proton donating ability of the CH group, the larger the stabilizing effect. This Perspective focuses on the consequence of this molecular force in the conformation of organic compounds and supramolecular chemistry. Implication of the CH/π hydrogen bond extends to the specificity of molecular recognition or selectivity in organic reactions, polymer science, surface phenomena and interactions involving proteins. Many problems, unsettled to date, will become clearer in the light of the CH/π paradigm.

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“…The evidence of proline as one of the components of DKP (compounds 1–3) was deduced from the presence of three broad methylene multiplets (δ H 1.25–3.65 ppm) in these compounds. Based on the analysis of 1-dimensional NMR data, COSY correlations and literature values, valine, isoleucine, and phenylalanine were identified as the second amino acid residue in compounds 1–3, respectively ( Jayatilake et al, 1996 ; Campo et al, 2009 ; Li et al, 2012 ; Ding et al, 2013 ; Jiang and Yang, 2013 ), while in compound 4 it was the combination of leucine and valine ( Ding et al, 2013 ). The configuration of the DKPs was determined by analysis of the NOESY spectrum and comparison with the optical rotations in the literature.…”

Section: Resultsmentioning

confidence: 99%

A Diketopiperazine, Cyclo-(L-Pro-L-Ile), Derived From Bacillus thuringiensis JCK-1233 Controls Pine Wilt Disease by Elicitation of Moderate Hypersensitive Reaction

et al. 2020

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Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

Cited by 16 publications

References 24 publications

Identification of Cryptic Products of the Gliotoxin Gene Cluster Using NMR-Based Comparative Metabolomics and a Model for Gliotoxin Biosynthesis

Identification of Cryptic Products of the Gliotoxin Gene Cluster Using NMR-Based Comparative Metabolomics and a Model for Gliotoxin Biosynthesis

The CH/π hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates

A Diketopiperazine, Cyclo-(L-Pro-L-Ile), Derived From Bacillus thuringiensis JCK-1233 Controls Pine Wilt Disease by Elicitation of Moderate Hypersensitive Reaction

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