A Series of ι-Trimethylammoniumalkylphosphonic Acids and Their Diethyl Ester Iodides¹

Deciphering the role of recurrent FAD-dependent enzymes in bacterial phosphonate catabolism

“…M 3 AEP became accessible from diethyl 2-(dimethylamino)-ethylphosphonate by alkylation with methyl iodide following an adapted literature procedure. 55 The trimethylated analogue ( R )-M 3 HAEP was obtained from ( R )-HAEP by methylation, while the ( R )-M 2 HAEP was accessible by an Eschweiler-Clark approach. The monomethylated derivative ( R )-M 1 HAEP was accessible from ( R )-diisopropyl (2-(1,3-dioxoisoindolin-2-yl)-1-hydroxyethyl)phosphonate 18 by using a tosylated intermediate to control the degree of methylation.…”

“…8 was dissolved in ethyl acetate (10 mL), washed with an aqueous solution of sodium hydroxide (20%, 3 × 5 mL), the organic phase was dried (MgSO 4 ), and concentrated in vacuo . The resulting residue was used for the synthesis of diethyl 2-( N,N,N -.trimethylammonium)-ethylphosphonate iodide ( 10 ; 330 mg, 0.94 mmol, 84%) following a literature procedure 55 m.p. 155-156°C; 1 H NMR (700.40 MHz, D 2 O) δ = 4.26-4.17 (m, 4H, 2 × O-CH 2 ) 3.65-3.59 (m, 2H, CH 2 -N), 3.17 (s, 9H, 3 × N-CH 3 ), 2.58-2.49 (m, 2H, CH 2 -P), 1.35 (t, 3 J H,H 7.1, 6H, 2 × O-CH 2 -C H 3 ); 13 C NMR (176.12 MHz, D 2 O) δ = 64.13 (d, 2 J C,P 6.7, 2C, 2 × O-CH 2 ), 60.22 (d, 2 J C,P 2.6, CH 2 -N), 52.57 (t, 1 J C,N 3.4, 3C, 3 × N-CH 3 .…”

Use of Column Chromatography for Quantitative Isolation of Mesoionic Pyrimidinium Betaines

“…UV-visible spectra were recorded on a double beam Spectro-pho-tometer of type SHIMADZU 061, using dioxane as solvent. 1 H NMR spectra were taken on AVANCE 300a, using deuterated solvents (DMSO-d 6 , CDCl 3 ) and tetramethylsilane (TMS) was employed as internal standard. IR spectra were recorded on JASCO 4100, samples in KBr pellets.…”

“…HE chemistry of betaines has become an interesting subject owing to their widespread applications in biological research, particularly for their metabolic rolesin living organisms [1]. Indeed, alkylbetaines are nowadays a class of products of increasing importance in many fields.…”

Isolation and Characterization of the N-Methyl Derivatives of 2-Aminoethylphosphonic Acid from the Sea Anemone, Anthopleura xanthogrammica*

“…The well-defined needle crystals melted at 252°dec. Myers and Jibril (1957) reported this compound to be a hemihydrate from alcohol, mp 250-252. Rosenthal (1958) states that this compound crystallizes from alcohol as the dihydrate but becomes the monohydrate when dried over phosphorus pentoxide at 50°under vacuum and becomes anhydrous when the drying temperature is 80°.…”