An improved synthesis of agaritine

Wallcave, Lawrence; Nagel, Donald; Raha, Chitta R.; Jae, Hwan-Soo; Bronczyk, Susan; Kupper, Robert; Tóth, Béla

doi:10.1021/jo01336a003

Cited by 28 publications

(16 citation statements)

References 1 publication

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“…Here, we report on the synthesis of 1 in 33% yield (based on 2) via the isolated 4-hydrazinobenzyl alcohol (3) by its condensation with 1-benzyl 5-hydrogen N-(benzyl-oxycarbony1)-L-glutamate (10). We also describe some properties of 3 which revealed its resistance against elimination of H,O, thus correcting literature claims [8] [9]. (3).…”

supporting

confidence: 73%

“…We also describe some properties of 3 which revealed its resistance against elimination of H,O, thus correcting literature claims [8] [9].…”

supporting

confidence: 72%

“…The product 11 is already known as an intermediate of the second synthesis [9] of agaritine (I), although it was not completely characterized by standard spectroscopy (see Exper. Purt).…”

Section: Synthesis Of Agaritine (1)mentioning

confidence: 99%

“…Applying these conditions for the debenzylation of I I using an Engelhard-or Fluka -10 % PdjC catalyst resulted only in L-glutamic acid 5-[2-(4-tolyl)hydrazide] (12) [8] [9]. The formation of this overreduced product could be avoided only by using a partially poisoned 10% Pd/C catalyst (see Exper.…”

Section: The Relative Slow Rate Of H/d-exchange Of Nh-c(2) Suggests Tmentioning

confidence: 99%

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Novel Synthesis of Agaritine, a 4‐Hydrazinobenzyl‐Alcohol Derivative Occurring in Agaricaceae

Datta

Hoesch

1987

Helvetica Chimica Acta

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The 4-hydrazinobenzyl alcohol (3) was prepared (58 YO) by diisobutylaluminiumhydride reduction of methyl 4-hydrazinobenzoate (4), whereas LiAIH, or LiBH, reduction of 4 proceeded further to yield (via intermediate 3) (4-to1yl)hydrazine (5). The alcohol 3 was stable under 0,-free conditions and exhibited no tendency to eliminate H20, neither thermally nor with H+ catalysis. Oxidation of 3 with Se02 yielded 4-(hydroxymethy1)benzenediazonium ion (S), identified by its azo coupling product 9 with 2-naphthol.

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supporting

confidence: 73%

“…We also describe some properties of 3 which revealed its resistance against elimination of H,O, thus correcting literature claims [8] [9].…”

supporting

confidence: 72%

“…The product 11 is already known as an intermediate of the second synthesis [9] of agaritine (I), although it was not completely characterized by standard spectroscopy (see Exper. Purt).…”

Section: Synthesis Of Agaritine (1)mentioning

confidence: 99%

Section: The Relative Slow Rate Of H/d-exchange Of Nh-c(2) Suggests Tmentioning

confidence: 99%

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Novel Synthesis of Agaritine, a 4‐Hydrazinobenzyl‐Alcohol Derivative Occurring in Agaricaceae

Datta

Hoesch

1987

Helvetica Chimica Acta

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“…Agaritine and HMPH were synthesized according to the methods of Wallcave et al (1979) and Hoesch et al (1987) with minor modifications. The purity of the synthetic agaritine was 495% by HPLC (254 nm) and 495% by 1 H-NMR (500 MHz, DMSO-d 6 ).…”

Section: Methodsmentioning

confidence: 99%

Determination of genotoxic phenylhydrazine agaritine in mushrooms using liquid chromatography–electrospray ionization tandem mass spectrometry

Kondo

Watanabe

Iwanaga

et al. 2006

Food Additives and Contaminants

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A new method with good sensitivity and specificity for detecting and quantifying genotoxic hydrazines, agaritine and 4-(hydroxymethyl)phenylhydrazine (HMPH), was developed using liquid chromatography-electrospray tandem mass spectrometry (MS). Synthetic agaritine and HMPH were structurally assigned by 1H-, 13C- and two-dimensional nuclear magnetic resonance (NMR) analysis (HMBC and HMQC), high-resolution fast-atom bombardment (HR-FAB) MS and time of flight (TOF) MS. The polar molecule agaritine was separated on an ODS column using 0.01% AcOH-MeOH (99:1, v/v) as an eluent with a simple solid-phase extraction cleanup. There were no interference peaks for any of the mushrooms. Agaricus spp. contained 1247 and 2017 microg g-1 agaritine. Other species of mushroom had no agaritine. Recoveries of agaritine from spiked mushroom samples were 60.3-114%. Intra-day precision values were 5.5 and 4.2%, and the inter-day precision values were acceptable (15.0 and 23.0%), as agaritine is unstable. The limit of quantification was 0.003 microg g-1. Even a trace amount of agaritine in mushrooms can, therefore, be determined using this method. We also directly analysed HMPH, an active free hydrazine form of genotoxic agaritine, and obtained direct evidence of its absence from mushrooms. A precursor ion scan confirmed that agaritine derivatives, which could exert similar toxicity, were absent. The results indicate that this specific and sensitive analytical method for detecting and quantifying agaritine and its derivatives could help evaluate the risk of mushroom hydrazines to humans.

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