Efficient Route to the Pineal Hormone Melatonin by Radical‐Based Indole Synthesis.

Thomson, Douglas W.; Commeureuc, Aurélien G. J.; Berlin, Stefan; Murphy, John A.

doi:10.1002/chin.200403226

Cited by 6 publications

(9 citation statements)

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“…Octa-2,7-diyn-1-ol (16), 29% yield. 1 H NMR (300 MHz, CDCl 3 , ): 1.63-1.75 (m, -CH 2 -, 2H), 1.94 (t, J = 2.6 Hz, CH, 1H), 2.09 (br s, -OH, 1H), 2.30 (m, -CH 2 -, 4H), 4.21 (t, J = 2.2 Hz, -CH 2 -, 2H); 13 C NMR (75 MHz, CDCl 3 , ): 17. 99, 24.80, 26.61, 51.24, 51.46, 79.34, 83.73, 85.35.…”

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Enhanced Chemical Stability of AdoMet Analogues for Improved Methyltransferase-Directed Labeling of DNA

et al. 2013

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Methyltransferases catalyze specific transfers of methyl groups from the ubiquitous cofactor S-adenosyl-l-methionine (AdoMet) to various nucleophilic positions in biopolymers like DNA, RNA, and proteins. We had previously described synthesis and application of AdoMet analogues carrying sulfonium-bound 4-substituted but-2-ynyl side chains for transfer by methyltransferases. Although useful in certain applications, these cofactor analogues exhibited short lifetimes in physiological buffers. Examination of the reaction kinetics and products showed that their fast inactivation followed a different pathway than observed for AdoMet and rather involved a pH-dependent addition of a water molecule to the side chain. This side reaction was eradicated by synthesis of a series of cofactor analogues in which the separation between an electronegative group and the triple bond was increased from one to three carbon units. The designed hex-2-ynyl moiety-based cofactor analogues with terminal amino, azide, or alkyne groups showed a markedly improved enzymatic transalkylation activity and proved well suitable for methyltransferase-directed sequence-specific labeling of DNA in vitro and in bacterial cell lysates.

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“…6-Azidohex-2-yn-1-ol (17), 70% yield. 1 H NMR (300 MHz, CDCl 3 , ): 1.81 (m, -CH 2 -and -OH, 3 H), 2.37 (tt, J = 6.9, 2.4 Hz, -C≡CCH 2 -, 2H), 3.44 (t, J = 6.9Hz, -CH 2 -, 2H), 4.28 (t, J = 2.4 Hz, -CH 2 -, 2H); 13 C NMR (75 MHz, CDCl 3 , ): 16.3, 27.9, 50.0, 51.5, 79.6, 84.7; IR: ν (cm -1 ) = 3350 (OH), 2223 (C≡C), 2100 ( N 3 ).…”

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Enhanced Chemical Stability of AdoMet Analogues for Improved Methyltransferase-Directed Labeling of DNA

et al. 2013

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“…Practically all melatonin supplements that are marketed are made from synthetic melatonin, although some of plant origin can be found (see below). Previously, melatonin was obtained from animal sources such as cows, but due to the risk of viral infection, synthetic production is often preferred, using a simple and very productive process [ 107 , 108 , 109 ]. There are various production methods involving several synthetic routes, as shown Table 3 .…”

Section: Sources Of Melatonin and Phytomelatoninmentioning

confidence: 99%

The Potential of Phytomelatonin as a Nutraceutical

Arnao

Hernández‐Ruíz

2018

Molecules

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Phytomelatonin (plant melatonin) is chemically related to the amino acid tryptophan and has many diverse properties. Phytomelatonin is an interesting compound due to its outstanding actions at the cellular and physiological level, especially its protective effect in plants exposed to diverse stress situations, while its vegetable origin offers many opportunities because it is a natural compound. We present an overview of its origin, its action in plants in general (particularly in plant species with high levels of phytomelatonin), and its possibilities for use as a nutraceutical with particular attention paid to the beneficial effects that it may have in human health. The differences between synthetic melatonin and phytomelatonin, according to its origin and purity, are presented. Finally, the current market for phytomelatonin and its limits and potentials are discussed.

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“…The first Mitsunobu intermediate product was obtained as a colorless solid in 52% yield using a reported procedure with all obtained spectra in agreement with the literature. 31 bis(tert-butoxycarbonyl)guanidine in dry tetrahydrofuran (THF) (5.0 mL). The mixture was cooled in an ice bath and diisopropyl azodicarboxylate (DIAD) (0.5 mL, 3.1 mmol) was added dropwise, and the reaction stirred for 16 h at room temperature under inert atmosphere.…”

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confidence: 99%

Improving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue

et al. 2018

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Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide-based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH2 sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-dLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Arg-mimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between S1 pockets of PACE4 and furin could be employed in the rational design of selective inhibitors.

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Efficient Route to the Pineal Hormone Melatonin by Radical‐Based Indole Synthesis.

Cited by 6 publications

References 1 publication

Enhanced Chemical Stability of AdoMet Analogues for Improved Methyltransferase-Directed Labeling of DNA

Enhanced Chemical Stability of AdoMet Analogues for Improved Methyltransferase-Directed Labeling of DNA

The Potential of Phytomelatonin as a Nutraceutical

Improving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue

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