High-Yield Syntheses of<i>N</i>-(2-Hydroxyethyl)-<i>N</i>-alkylglycine Derivatives by Reaction of Ethanolamines with Glyoxal

The ephedrine derivative, (H2ceph), yields [Cu(Hceph)2], showing a CH...Cu(II) agostic interaction; while in the analogous compound [Cu(Hcpse)2], with pseudoephedrine (H2cpse), that interaction is absent, despite the fact that these two diasteromers differ only in the orientation of the methyl and phenyl groups: erythro in H2ceph and threo in H2cpse. The X-ray crystal structure of [Cu(Hceph)2], indicates a Cu...HC length of 2.454 A and the theoretical study reveals the formation of a Cu...HC bond since the associated electronic density shows both a bond critical point and a bond ring critical point.

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“…1). 5 It has been observed that they give place to stereoselective coordination compounds. 6 for II.…”

mentioning

confidence: 99%

On the CH⋯Cu agostic interaction: chiral copper(ii) compounds with ephedrine and pseudoephedrine derivatives

et al. 2005

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“…When compounds 2a-2e were treated with two equivalents of sodium cyanide and heated in water or different water/solvent mixtures to a temperature of 40 uC, the expected cyanide induced hydrolysis reaction took place, giving the N-substituted N-2-hydroxyethylglycine sodium salts 3a-3e (Scheme 1) in yields between 66 and 94%. 10 It was noticeable that the n-butyl, 2b (66%), and tert-butyl, 2c (80%), Strecker scavengers were the less efficient for the scavenging action. It is also worth mentioning that in the mining industry, most of the washing operations are carriers of harmful ions, where the water molecules physically scavenge the cyanide counterparts.…”

Section: Resultsmentioning

confidence: 97%

Strecker intermediates as non-pollutant scavengers for cyanides

Godínez-Salomón

Hallen-López

Höpfl³

et al. 2005

Green Chem.

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“…Easy syntheses of N-alkylated amino acids allow the identification of natural products in crude extracts from plants where isolation of the pure natural product is difficult. Although the mechanism is unclear (Amadori or intramolecular Cannizarro rearrangements), the reaction of secondary amines with aqueous glyoxal gives N,N-dialkyl glycines in good yield (Scheme 1) (Farfán et al 1987). Treatment of the iminosugars DMDP 1, DAB 7, and galacto-DMDP 10 with aqueous glyoxal at 70 °C for 14-17 h gave the corresponding acetic acids 5, 8, and 11 in yields of 100%, 82%, and 99%, respectively, and were readily isolated with a minimum of purification.…”

Section: Synthesis Of Pyrrolidine N-acetic Acids From Unprotected Imimentioning

confidence: 99%

Isolation from Stevia rebaudiana of DMDP acetic acid, a novel iminosugar amino acid: synthesis and glycosidase inhibition profile of glycine and β-alanine pyrrolidine amino acids

Martínez¹,

Jenkinson²,

Nakagawa

et al. 2019

Amino Acids

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DMDP acetic acid [N-carboxymethyl-2,5-dideoxy-2,5-imino-d-mannitol] 5 from Stevia rebaudiana is the first isolated natural amino acid derived from iminosugars bearing an N-alkyl acid side chain; it is clear from GCMS studies that such derivatives with acetic and propionic acids are common in a broad range of plants including mulberry, Baphia, and English bluebells, but that they are very difficult to purify. Reaction of unprotected pyrrolidine iminosugars with aqueous glyoxal gives the corresponding N-acetic acids in very high yield; Michael addition of both pyrrolidine and piperidine iminosugars and that of polyhydroxylated prolines to tert-butyl acrylate give the corresponding N-propionic acids in which the amino group of β-alanine is incorporated into the heterocyclic ring. These easy syntheses allow the identification of this new class of amino acid in plant extracts and provide pure samples for biological evaluation. DMDP N-acetic and propionic acids are potent α-galactosidase inhibitors in contrast to potent β-galactosidase inhibition by DMDP.

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High-Yield Syntheses ofN-(2-Hydroxyethyl)-N-alkylglycine Derivatives by Reaction of Ethanolamines with Glyoxal

Cited by 17 publications

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On the CH⋯Cu agostic interaction: chiral copper(ii) compounds with ephedrine and pseudoephedrine derivatives

On the CH⋯Cu agostic interaction: chiral copper(ii) compounds with ephedrine and pseudoephedrine derivatives

Strecker intermediates as non-pollutant scavengers for cyanides

Isolation from Stevia rebaudiana of DMDP acetic acid, a novel iminosugar amino acid: synthesis and glycosidase inhibition profile of glycine and β-alanine pyrrolidine amino acids

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