Indoles: Industrial, Agricultural and Over-the-Counter Uses

Barden, Timothy C.

doi:10.1007/7081_2010_48

Cited by 120 publications

(38 citation statements)

References 29 publications

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“…[2,3] The indole structure is also ab uildingb lock of am ultitude of synthetic compounds [4] that are not only used as pharmaceutical products but are also broadly applied in various technical branches. [5] The Catharanthus alkaloids and othern aturalm onoterpene indolea lkaloids are biosynthesized from tryptamine and secologanin, an iridoid glycoside, to form strictosidine. [6,7] Apart from monoterpenes, few alternative buildingb locks have been reported to be involved in indole alkaloid biosynthesis.…”

Section: Introductionmentioning

confidence: 99%

Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids

et al. 2016

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Nudicaulins are a group of indole alkaloid glycosides responsible for the color of yellow petals of Papaver nudicaule (Iceland poppy). The unique aglycone scaffold of these alkaloids attracted our interest as one of the most unusual flavonoid‐indole hybrid structures that occur in nature. Stable isotope labeling experiments with sliced petals identified free indole, but not tryptamine or l‐tryptophan, as one of the two key biosynthetic precursors of the nudicaulin aglycone. Pelargonidin was identified as the second key precursor, contributing the polyphenolic unit to the nudicaulin molecule. This finding was inferred from the temporary accumulation of pelargonidin glycosides in the petals during flower bud development and a drop at the point in time when nudicaulin levels start to increase. The precursor‐directed incorporation of cyanidin into a new 3′‐hydroxynudicaulin strongly supports the hypothesis that anthocyanins are involved in the biosynthesis of nudicaulins.

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Section: Introductionmentioning

confidence: 99%

Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids

et al. 2016

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“…IGPS is a validated antibiotic target, including for Mycobacterium tuberculosis , and has been frequently used as a starting protein framework in the engineering of novel enzyme activities . We have suggested that IGPS‐based catalysts could also find utility in producing new indole derivatives; the indole ring is an extremely prevalent structure in pharmaceutical, agricultural and other industrial compounds . Recently, our laboratory revised the chemical mechanism for IGPS (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…4,5 We have suggested that IGPS-based catalysts could also find utility in producing new indole derivatives; the indole ring is an extremely prevalent structure in pharmaceutical, agricultural and other industrial compounds. 6 Recently, our laboratory revised the chemical mechanism for IGPS ( Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Loop‐loop interactions govern multiple steps in indole‐3‐glycerol phosphate synthase catalysis

et al. 2014

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Substrate binding, product release, and likely chemical catalysis in the tryptophan biosynthetic enzyme indole-3-glycerol phosphate synthase (IGPS) are dependent on the structural dynamics of the b1a1 active-site loop. Statistical coupling analysis and molecular dynamic simulations had previously indicated that covarying residues in the b1a1 and b2a2 loops, corresponding to Arg54 and Asn90, respectively, in the Sulfolobus sulfataricus enzyme (ssIGPS), are likely important for coordinating functional motions of these loops. To test this hypothesis, we characterized site mutants at these positions for changes in catalytic function, protein stability and structural dynamics for the thermophilic ssIGPS enzyme. Although there were only modest changes in the overall steady-state kinetic parameters, solvent viscosity and solvent deuterium kinetic isotope effects indicated that these amino acid substitutions change the identity of the rate-determining step across multiple temperatures. Surprisingly, the N90A substitution had a dramatic effect on the general acid/base catalysis of the dehydration step, as indicated by the loss of the descending limb in the pH rate profile, which we had previously assigned to Lys53 on the b1a1 loop. These changes in enzyme function are accompanied with a quenching of ps-ns and ms-ms timescale motions in the b1a1 loop as measured by nuclear magnetic resonance studies. Altogether, our studies provide structural, dynamic and functional rationales for the coevolution of residues on the b1a1 and b2a2 loops, and highlight the multiple roles that the b1a1 loop plays in IGPS catalysis. Thus, substitution of covarying residues in the active-site b1a1 and b2a2 loops of indole-3-glycerol phosphate synthase results in functional, structural, and dynamic changes, highlighting the multiple roles that the b1a1 loop plays in enzyme catalysis and the importance of regulating the structural dynamics of this loop through noncovalent interactions with nearby structural elements.

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“…The indole moiety is one of the most common heterocycles in nature and is considered a "privileged" structure involved in a plethora of compounds within the pharmaceutical, agricultural, and materials science industries (1). As such, the synthesis of indole and its many derivatives remains a very active area of research (2).…”

mentioning

confidence: 99%

Functional Identification of the General Acid and Base in the Dehydration Step of Indole-3-glycerol Phosphate Synthase Catalysis

Zaccardi

Yezdimer

Boehr

2013

Journal of Biological Chemistry

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Background: Bacteria require the enzyme indole-3-glycerol phosphate synthase for the production of Trp. Results: Glu-51 and Lys-53 are identified as the base and acid acting in the dehydration step of enzyme catalysis. Conclusion: Ring closure and dehydration steps are catalyzed by distinct active-site surfaces. Significance: Enzyme inhibitors targeted against these active-site surfaces may serve as novel antibiotics.

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Indoles: Industrial, Agricultural and Over-the-Counter Uses

Cited by 120 publications

References 29 publications

Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids

Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids

Loop‐loop interactions govern multiple steps in indole‐3‐glycerol phosphate synthase catalysis

Functional Identification of the General Acid and Base in the Dehydration Step of Indole-3-glycerol Phosphate Synthase Catalysis

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