Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts

Jin, Lei; Zhao, Shuai; Chen, Xin

doi:10.3390/molecules23061421

Cited by 6 publications

(3 citation statements)

References 46 publications

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“…For hydroxy‐containing building block 8 , a modified version of our own synthesis can be carried out starting from 13 C 2 ‐glycine 6 instead of standard glycine 14 . The allylglycine subunit 7 could be traced back to 13 C 2 ‐bromoacetic acid 5 and obtained by a classic phase‐transfer catalyzed asymmetric amino acid synthesis 16–30 …”

Section: Introductionmentioning

confidence: 99%

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Total synthesis of [¹³C₂]‐labeled phytosiderophores of the mugineic and avenic acid families

Kratena,

Draskovits,

Biedermann

et al. 2023

Labelled Comp Radiopharmac

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We, herein, report the synthesis of 13C2‐labeled natural products from the mugineic acid and avenic acid family. These phytosiderophores (“plant iron carriers”) are built up from non‐proteinogenic amino acids and play a key role in micronutrient uptake in gramineous plants. In this work, two central building blocks are prepared from labeled starting materials (13C2‐bromoacetic acid, 13C2‐glycine) and further employed in our recently reported divergent, branched synthetic strategy delivering eight isotopically labeled phytosiderophores. The required labeled building blocks (13C2‐l‐allylglycine and a related hydroxylated derivative) were prepared via enantioselective phase‐transfer catalysis and enantio‐ and diastereoselective aldol condensation with a chiral auxiliary, respectively, both potentially valuable themselves for other synthetic routes toward labeled (natural) products.

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Section: Introductionmentioning

confidence: 99%

“…14 The allylglycine subunit 7 could be traced back to 13 C 2 -bromoacetic acid 5 and obtained by a classic phase-transfer catalyzed asymmetric amino acid synthesis. [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of [¹³C₂]‐labeled phytosiderophores of the mugineic and avenic acid families

Kratena,

Draskovits,

Biedermann

et al. 2023

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

show abstract

“…Various types of PTC have been utilized, the most common ones being quaternary ammonium salts, with the tetraalkylammonium ion acting as the counter ion of the reactive anion. These quaternary ammonium salts are applied in liquid-liquid phase-transfer catalysis (Annunziata et al 2000;Chinchílla et al 2000;Denmark et al 2011;Waser et al 2012;Jia et al 2015;Jin et al 2018).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel polymer quaternary ammonium salt derived from glucose as a phase transfer catalyst

et al. 2022

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Abstract. Alrubaie I, Salim AT, Majeed MM, Radhi AJ. 2022. Synthesis of novel polymer quaternary ammonium salt derived from glucose as a phase transfer catalyst. Nusantara Bioscience 14: 25-33. Some new polymer containing quaternary ammonium salts based-carbohydrate starting from methyl-4,6-O-benzylidene-glucopyranoside have been prepared. The ammonium groups are connected to the glucose structure in various positions (2 and 3). Our synthesis used methyl-4,6-O-benzylidene-a-D-glucopyranoside through nucleophilic reagents to produce the main intermediates. The monomer glucose- quaternary ammonium salts are immobilized on the polyvinyl azide to give the final structure of the Polymer-Supported quaternary ammonium salts. In certain new kinds of phase transfer catalysts, the effectiveness of the polymer glucose-quaternary ammonium salts was tested in the Williamson etherification. The ether synthesis is a typical example of using a phase transfer catalyst. The reactions were performed in a liquid-liquid two-phase system, applying a mixture of toluene and 50% solution of aqueous sodium hydroxide in the presence of a 20 mg/mmol catalyst (compound 9). Compared to other derivatives, the reaction of 4-nitrophenol with dibromoethylene gives the highest yields. On the other hand, compound 9 with the C16 chain gives high activity in the phase transfer catalyst.

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Allosteric Inhibition of the β₂‐Adrenergic Receptor: Design and Synthesis of Cmpd‐15 Analogs

Ye,

Li,

Luo

et al. 2024

Chemistry & Biodiversity

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We designed and synthesized 27 new amide and dipeptide derivatives containing a substituted phenylalanine as negative allosteric modulators (NAMs) for the beta‐2 adrenergic receptor (β2AR). These analogs aimed to improve the activity of our lead compound, Cmpd‐15, by introducing variations in three key regions: the meta‐bromobenzyl methylbenzamide (S1), para‐formamidophenylalanine (S2), and 1‐cyclohexyl‐1‐phenylacetyl (S3) groups. The synthesis involved the Pd‐catalyzed β‐C(sp3)‐H arylation of N‐acetylglycine with 1‐iodo‐4‐substituent‐benzenes as the key step. GloSensor cAMP accumulation assay revealed that six analogs (A1, C5, C6, C13, C15 and C17) surpass Cmpd‐15 in β2AR allosteric function. This highlights the crucial role of the S1 region (meta‐bromobenzyl methylbenzamide) in β2AR allostery while suggesting potential replaceability of the S2 region (para‐formamidophenylalanine). These findings serve as a valuable springboard for further optimizing Cmpd‐15, potentially leading to smaller, more active, and more stable β2AR‐targeting NAMs.

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Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts

Cited by 6 publications

References 46 publications

Total synthesis of [¹³C₂]‐labeled phytosiderophores of the mugineic and avenic acid families

Total synthesis of [¹³C₂]‐labeled phytosiderophores of the mugineic and avenic acid families

Synthesis of novel polymer quaternary ammonium salt derived from glucose as a phase transfer catalyst

Allosteric Inhibition of the β₂‐Adrenergic Receptor: Design and Synthesis of Cmpd‐15 Analogs

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Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts

Cited by 6 publications

References 46 publications

Total synthesis of [13C2]‐labeled phytosiderophores of the mugineic and avenic acid families

Total synthesis of [13C2]‐labeled phytosiderophores of the mugineic and avenic acid families

Synthesis of novel polymer quaternary ammonium salt derived from glucose as a phase transfer catalyst

Allosteric Inhibition of the β2‐Adrenergic Receptor: Design and Synthesis of Cmpd‐15 Analogs

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Product

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Total synthesis of [¹³C₂]‐labeled phytosiderophores of the mugineic and avenic acid families

Total synthesis of [¹³C₂]‐labeled phytosiderophores of the mugineic and avenic acid families

Allosteric Inhibition of the β₂‐Adrenergic Receptor: Design and Synthesis of Cmpd‐15 Analogs