A Novel Method for Biomimetic Synthesis of Mannich Bases

Guo, Yuan; An, Jing; Lu, Zhenhuan; Peng, Meng-Jiao

doi:10.1002/cjoc.201100628

Cited by 3 publications

(2 citation statements)

References 20 publications

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“…On the contrary, the methyl ketones 2-nonanone and 2-undecanone, coming from the same metabolic pathway (Park et al, 2012 ), showed strong fungal growth inhibition. Methyl ketones, commonly found in nature as constituent of essential oils of several plants and produced by bacteria, fungi, insects (Cavill et al, 1956 ; Cavill and Hinterberger, 1960 ; Bernardi et al, 1967 ; Moser et al, 1968 ), and mammalian cells (Forney and Markovetz, 1971 ), present a variety of biological properties and potential commercial exploitations (Forney and Markovetz, 1971 ; Bolster et al, 2001 ; Antonious et al, 2003 ; Guo et al, 2008 ; Shi et al, 2008 ; Zhu and Hua, 2009 ). For example, 2-nonanone, released by red raspberries and strawberries during ripening, was demonstrated to inhibit postharvest decay fungi in strawberry fruit (Vaughn et al, 1993 ) and both 2-nonanone and 2-undecanone from soil bacteria have nematicidal action (Gu et al, 2007 ).…”

Section: Discussionmentioning

confidence: 99%

Biocide effects of volatile organic compounds produced by potential biocontrol rhizobacteria on Sclerotinia sclerotiorum

et al. 2015

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Six rhizobacteria isolated from common bean and able to protect bean plants from the common bacterial blight (CBB) causal agent, were in vitro evaluated for their potential antifungal effects toward different plant pathogenic fungi, mostly soil-borne. By dual culture assays, the above bacteria resulted producing diffusible and volatile metabolites which inhibited the growth of the majority of the pathogens under study. In particular, the latter substances highly affected the mycelium growth of Sclerotinia sclerotiorum strains, one of which was selected for further studies either on mycelium or sclerotia. Gas chromatographic analysis of the bacterial volatiles led to the identification of an array of volatile organic compounds (VOCs). Time course studies showed the modification of the VOCs profile along a period of 5 days. In order to evaluate the single detected VOC effects on fungal growth, some of the pure compounds were tested on S. sclerotiorum mycelium and their minimal inhibitory quantities were determined. Similarly, the minimal inhibitory quantities on sclerotia germination were also defined. Moreover, observations by light and transmission electron microscopes highlighted hyphae cytoplasm granulation and ultrastructural alterations at cell organelles, mostly membranes, mitochondria, and endoplasmic reticulum. The membranes appeared one of the primary targets of bacterial volatiles, as confirmed by hemolytic activity observed for the majority of pure VOCs. However, of interest is the alteration observed on mitochondria as well.

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Section: Discussionmentioning

confidence: 99%

Biocide effects of volatile organic compounds produced by potential biocontrol rhizobacteria on Sclerotinia sclerotiorum

et al. 2015

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“…β-keto fatty acids are also readily decarboxylated in vitro by brief exposure to heat under acidic conditions [23]. MKs are widely used in the flavouring and fragrance industries and as blending agents for biofuels, while 3-hydroxy fatty acids have applications as components of lubricants and surfactants [26][27][28][29][30][31][32]. To date, medium-chain methylketones and 3-hydroxy fatty acids are largely sourced from fossil hydrocarbons, and engineering a sustainable means of producing them remains a challenge [26].…”

Section: Introductionmentioning

confidence: 99%

Determinants of substrate specificity in a catalytically diverse family of acyl-ACP thioesterases from plants

Kalinger

Rowland

2023

BMC Plant Biol

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Background ACYL-LIPID THIOESTERASES (ALTs) are a subclass of plastid-localized, fatty acyl-acyl carrier protein (ACP) thioesterase enzymes from plants. They belong to the single hot dog-fold protein family. ALT enzymes generate medium-chain (C6-C14) and C16 fatty acids, methylketone precursors (β-keto fatty acids), and 3-hydroxy fatty acids when expressed heterologously in E. coli. The diverse substrate chain-length and oxidation state preferences of ALTs set them apart from other plant acyl-ACP thioesterases, and ALTs show promise as metabolic engineering tools to produce high-value medium-chain fatty acids and methylketones in bacterial or plant systems. Here, we used a targeted motif-swapping approach to explore connections between ALT protein sequence and substrate specificity. Guided by comparative motif searches and computational modelling, we exchanged regions of amino acid sequence between ALT-type thioesterases from Arabidopsis thaliana, Medicago truncatula, and Zea mays to create chimeric ALT proteins. Results Comparing the activity profiles of chimeric ALTs in E. coli to their wild-type counterparts led to the identification of interacting regions within the thioesterase domain that shape substrate specificity and enzyme activity. Notably, the presence of a 31-CQH[G/C]RH-36 motif on the central α-helix was shown to shift chain-length specificity towards 12–14 carbon chains, and to be a core determinant of substrate specificity in ALT-type thioesterases with preference for 12–14 carbon 3-hydroxyacyl- and β-ketoacyl-ACP substrates. For an ALT containing this motif to be functional, an additional 108-KXXA-111 motif and compatible sequence spanning aa77–93 of the surrounding β-sheet must also be present, demonstrating that interactions between residues in these regions of the catalytic domain are critical to thioesterase activity. The behaviour of chimeric enzymes in E. coli also indicated that aa77–93 play a significant role in dictating whether an ALT will prefer ≤10-carbon or ≥ 12-carbon acyl chain-lengths, and aa91–96 influence selectivity for substrates of fully or partially reduced oxidation states. Additionally, aa64–67 on the hot dog-fold β-sheet were shown to be important for enabling an ALT to act on 3-hydroxy fatty acyl-ACP substrates. Conclusions By revealing connections between thioesterase sequence and substrate specificity, this study is an advancement towards engineering recombinant ALTs with product profiles suited for specific applications.

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ChemInform Abstract: A Novel Method for Biomimetic Synthesis of Mannich Bases.

Guo

et al. 2012

ChemInform

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A Novel Method for Biomimetic Synthesis of Mannich Bases

Cited by 3 publications

References 20 publications

Biocide effects of volatile organic compounds produced by potential biocontrol rhizobacteria on Sclerotinia sclerotiorum

Biocide effects of volatile organic compounds produced by potential biocontrol rhizobacteria on Sclerotinia sclerotiorum

Determinants of substrate specificity in a catalytically diverse family of acyl-ACP thioesterases from plants

ChemInform Abstract: A Novel Method for Biomimetic Synthesis of Mannich Bases.

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