A new method of quaternizing amines and its use in amino acid and peptide chemistry

Chen, Francis C. M.; Benoiton, N. Leo

doi:10.1139/v76-475

Cited by 96 publications

(56 citation statements)

References 2 publications

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“…For NMR analyses, dried total cell extracts were recorded with a Bruker AVANCE 500 spectrometer ( 1 H: 500.13 MHz; 13 C: 125.8 MHz). The obtained spectra were compared with synthetic homoserine betaine, which was obtained by the protocol of Chen and Benoiton (22). The E. coli wild-type MC4100 and mutant FF4169 were cultivated in M63 minimal medium (40) with 400 mM NaCl and 0.4% glucose to study the osmoprotective effect of homoserine betaine.…”

Section: Methodsmentioning

confidence: 99%

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Trimethylated homoserine functions as the major compatible solute in the globally significant oceanic cyanobacterium Trichodesmium

Pade

Michalik

Ruth

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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The oceanic N 2 -fixing cyanobacterium Trichodesmium spp. form extensive surface blooms and contribute significantly to marine carbon and nitrogen cycles in the oligotrophic subtropical and tropical oceans. Trichodesmium grows in salinities from 27 to 43 parts per thousand (ppt), yet its salt acclimation strategy remains enigmatic because the genome of Trichodesmium erythraeum strain IMS101 lacks all genes for the biosynthesis of any known compatible solute. Using NMR and liquid chromatography coupled to mass spectroscopy, we identified the main compatible solute in T. erythraeum strain IMS101 as the quaternary ammonium compound N,N,N-trimethyl homoserine (or homoserine betaine) and elucidated its biosynthetic pathway. The identification of this compatible solute explains how Trichodesmium spp. can thrive in the marine system at varying salinities and provides further insight into the diversity of microbial salt acclimation.salt stress | compatible solute | cyanobacteria

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Section: Methodsmentioning

confidence: 99%

“…To verify the structural analysis, homoserine betaine was synthesized from L-homoserine by using methyliodide as described by Chen and Benoiton (22). The synthesized standard compound showed the same retention time and MS pattern as the native compatible solute in extracts from Trichodesmium after HPLC-MS analysis (Fig.…”

Section: Significancementioning

confidence: 99%

Trimethylated homoserine functions as the major compatible solute in the globally significant oceanic cyanobacterium Trichodesmium

Pade

Michalik

Ruth

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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“…As hercynine was not commercially available, it was prepared by a modified heterogeneous phase reaction employing iodomethane as the methylation agent in the presence of KHCO 3 [24,25]. Also deuterated hercynine (EH-d 9 ) was prepared in the same way by substituting iodomethane with deuterated iodomethane (methyl-d 3 iodide).…”

Section: Preparation Of Ergothioneine Disulfidementioning

confidence: 99%

An uncommon redox behavior sheds light on the cellular antioxidant properties of ergothioneine

Servillo

Castaldo

Casale

et al. 2015

Free Radical Biology and Medicine

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“…Sulfocholine was prepared from 2-(methylthio)ethanol by the method of Tremblay and Kates (1979). Other choline analogs were prepared by reacting alkyl iodides with amines according to the method of Chen and Benoiton (1976), except that KHCO, was omitted from the tetraethanolamine synthesis. These analogs and their precursors are listed in Table I.…”

Section: Choline Analogs and Affinity Adsorbentsmentioning

confidence: 99%

Assay, Purification, and Partial Characterization of Choline Monooxygenase from Spinach

1995

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l h e osmoprotectant glycine betaine is synthesized via the pathway choline -+ betaine aldehyde + glycine betaine. I n spinach (Spinacia oleracea), the first step is catalyzed by choline monooxygenase (CMO), and the second is catalyzed by betaine aldehyde dehydrogenase. Because betaine aldehyde is unstable and not easily detected, we developed a coupled radiometric assay for CMO.['4C]Choline is used as substrate; NAD+ and betaine aldehyde dehydrogenase prepared from Escherichia coli are added to oxidize [l4C1betaine aldehyde to ['4Clglycine betaine, which is isolated by ion exchange. The assay was used i n the purification of CMO from leaves of salinized spinach. The 1 O-step procedure included polyethylene glycol precipitation, polyethyleneimine precipitation, hydrophobic interaction, anion exchange on choline-Sepharose, dimethyldiethanolamine-Sepharose, and Mono Q, hydroxyapatite, gel filtration, and sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Following gel filtration, overall purification was about CMO is a homodimer. CMO preparations were red-brown, showed absorption maxima at 329 and 459 nm, and lost color upon dithionite addition, suggesting that CMO is an iron-sulfur protein.

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A new method of quaternizing amines and its use in amino acid and peptide chemistry

Abstract: Methyl iodide and potassium bicarbonate in methanol is presented as a mild, efficient, and selective reagent for the quaternization of amino groups. It does not attack hydroxyl groups. Its use with amino acids, derivatives of lysine, and small peptides is described.

Cited by 96 publications

References 2 publications

Trimethylated homoserine functions as the major compatible solute in the globally significant oceanic cyanobacterium Trichodesmium

Trimethylated homoserine functions as the major compatible solute in the globally significant oceanic cyanobacterium Trichodesmium

An uncommon redox behavior sheds light on the cellular antioxidant properties of ergothioneine

Assay, Purification, and Partial Characterization of Choline Monooxygenase from Spinach

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