A new silylation reagent for amino acids bis (trimethylsilyl)trifluoroacetamide (BSTFA)

Stalling, Davis L.; Gehrke, Charles W.; Zumwalt, Robert W.

doi:10.1016/0006-291x(68)90523-8

Cited by 121 publications

(29 citation statements)

References 6 publications

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“…Since both compounds contain polar hydrogen bonding groups, i.e., hydroxyl or carboxyl, which are not adequately volatile for GC, they were derivatized with BSTFA to generate volatile TMS derivatives. 17 …”

Section: Resultsmentioning

confidence: 99%

Metabolism of 4-Hydroxy-7-oxo-5-heptenoic Acid (HOHA) Lactone by Retinal Pigmented Epithelial Cells

Wang

Linetsky

Guo

et al. 2016

Chem. Res. Toxicol.

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4-Hydroxy-7-oxo-5-heptenic acid (HOHA)-lactone is a biologically active oxidative truncation product released (t1/2 = 30 min at 37 °C) by non-enzymatic transesterification/deacylation from docosahexaenoate lipids. We now report that HOHA-lactone readily diffuses into retinal pigmented epithelial (RPE) cells where it is metabolized. A reduced glutathione (GSH) Michael adduct of HOHA-lactone is the most prominent metabolite detected by LC-MS in both the extracellular medium and cell lysates. This molecule appeared inside of ARPE-19 cells within seconds after exposure to HOHA-lactone. The intracellular level reached a maximum concentration at 30 min and then decreased with concomitant increases in its level in the extracellular medium, thus revealing a unidirectional export of the reduced GSH-HOHA-lactone adduct from the cytosol to extracellular medium. This metabolism is likely to modulate the involvement of HOHA-lactone in the pathogenesis of human diseases. HOHA-lactone is biologically active, e.g., low concentrations (0.1-1 μM) induce secretion of vascular endothelial growth factor (VEGF) from ARPE-19 cells. HOHA-lactone is also a precursor of 2-(ω-carboxyethyl)pyrrole (CEP) derivatives of primary amino groups in proteins and ethanolamine phospholipids that have significant pathological and physiological relevance to age-related macular degeneration (AMD), cancer and wound healing. Both HOHA-lactone and the derived CEP can contribute to the angiogenesis that defines the neovascular “wet” form of AMD and that promotes the growth of tumors. While GSH depletion can increase the lethality of radiotherapy, because it will impair the metabolism of HOHA-lactone, the present study suggests that GSH depletion will also increase levels of HOHA-lactone and CEP that may promote recurrence of tumor growth.

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Section: Resultsmentioning

confidence: 99%

Metabolism of 4-Hydroxy-7-oxo-5-heptenoic Acid (HOHA) Lactone by Retinal Pigmented Epithelial Cells

Wang

Linetsky

Guo

et al. 2016

Chem. Res. Toxicol.

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“…Tertiary amines were analyzed directly. One other Panama species, I. laurina, was analyzed by gas chromatography after derivatization (49). Several individuals from each species were analyzed separately and, in all cases, chemical profiles based on presence/absence of compounds were identical within a species.…”

Section: Methodsmentioning

confidence: 99%

The evolution of antiherbivore defenses and their contribution to species coexistence in the tropical tree genusInga

Kursar

Dexter²,

Lokvam

et al. 2009

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

268

353

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Plants and their herbivores constitute more than half of the organisms in tropical forests. Therefore, a better understanding of the evolution of plant defenses against their herbivores may be central for our understanding of tropical biodiversity. Here, we address the evolution of antiherbivore defenses and their possible contribution to coexistence in the Neotropical tree genus Inga (Fabaceae). Inga has >300 species, has radiated recently, and is frequently one of the most diverse and abundant genera at a given site. For 37 species from Panama and Peru we characterized developmental, ant, and chemical defenses against herbivores. We found extensive variation in defenses, but little evidence of phylogenetic signal. Furthermore, in a multivariate analysis, developmental, ant, and chemical defenses varied independently (were orthogonal) and appear to have evolved independently of each other. Our results are consistent with strong selection for divergent defensive traits, presumably mediated by herbivores. In an analysis of community assembly, we found that Inga species co-occurring as neighbors are more different in antiherbivore defenses than random, suggesting that possessing a rare defense phenotype increases fitness. These results imply that interactions with herbivores may be an important axis of niche differentiation that permits the coexistence of many species of Inga within a single site. Interactions between plants and their herbivores likely play a key role in the generation and maintenance of the conspicuously high plant diversity in the tropics. plant defenses ͉ community assembly ͉ phylogenetic signal ͉ herbivory ͉ tropical diversity

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“…This procedure was repeated two or three times to remove traces of water. Equal volumes (usually 543 10-20 ul) of dimethylformamide and bis(trimethylsilyl)trifluoroacetamide (25) were added to the residue. The reaction vessel was fitted with a small cold finger to reduce evaporation during silylation, and the mixture was maintained at 60 C for 2 to 4 hr.…”

mentioning

confidence: 99%

Gas-Liquid Chromatographic Isolation of Cytokinins from Natural Sources

Upper¹,

Helgeson²,

Kemp³

et al. 1970

Plant Physiol.

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Gas-liquid chromatographic retention times for 20 purines or purine nucleosides, 14 of which are highly active cytokinins, are reported. With one exception, all of the naturally occurring cytokinins are separated.Ethyl acetate extraction of yeast transfer RNA hydrolysates and of culture filtrates of Agrobacterium tumefaciens gave sufficient concentration of the naturally occurring cytokinins for immediate gas-liquid chromatography. This procedure permitted the detection of 6-(3-methyl-2-butenylamino) -9 -#, D -ribofuranosylpurine in yeast transfer RNA extracts. An active cytokinin was isolated from A. tumefaciens culture filtrates and was tentatively identified as 6-(3-methyl-2-butenylamino)purine.The biosynthesis and mechanism of action of cytokinins in higher plants are currently the subjects of considerable interest (see recent reviews 5,10,16,17). Since progress in this area has been limited by tedious purifications and time-consuming biological assays, an analytical and preparative method is needed which would quantitatively and qualitatively measure the cytokinins present both in t-RNA and in soluble fractions. Gas-liquid chromatographic analysis would provide such a system, if it could be made applicable to extracts of biological materials. GLC' detection and isolation have been utilized in the identification of the gibberellins (3). Recently, Davis et al. (4) have extended the use of GLC to detection of indoleacetic acid and abscisic acid. Trimethylsilyl derivatives of purines, pyrimidines, nucleosides, and nucleotides have been utilized in GLC studies (7,8,23) and in coupled gas-liquid chromatographic-mass spectrometric studies (19). Conditions for GLC of TMS cytokinins have been published (21).We utilized two natural sources of cytokinins: yeast t-RNA and culture filtrates from Agrobacterium tumefaciens, the causal organism of crown gall. Yeast t-RNA is known to contain the cytokinin 6-(3-methyl-2-butenylamino)-9-3,D-ribofuranosylpurine in approximately 0.065 mole % of the total bases (22). Braun and Abbreviations: GLC, gas-liquid chromatography; TMS, trimethylsilyl-; 2iP and 2iPA, 6-(3-methyl-2-butenylamino)purine and its 9-3,D-ribofuranoside, respectively; DMF, dimethylformamide; BSTFA, bis(trimethylsilyl)trifluoroacetamide; 2MS and 2MSA,methyl-2-butenylamino)-2-methylthiopurine and its 9-,B,D-ribofuranoside, respectively; 3iPA, 6-(3-methyl-3-butenylamino)-9,B,D-ribofuranosylpurine.his co-workers recently demonstrated that bacteria-free gal tissue produced under the influence of A. tumefaciens contains cytokinin-like activity (27). The structure of the substance(s) from the gall tissue remains to be elucidated. Klimbt (13) reported the isolation of material with cytokinin-like biological activity from extracts of A. tumefaciens culture filtrates. His material had an ultraviolet spectrum suggestive of a purine and could not be separated from 2iP by paper chromatography. The highly active cytokinin, 6-(3-methyl-2-butenylamino)purine was identified after isolation from culture filtrates of Coryn...

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A new silylation reagent for amino acids bis (trimethylsilyl)trifluoroacetamide (BSTFA)

Cited by 121 publications

References 6 publications

Metabolism of 4-Hydroxy-7-oxo-5-heptenoic Acid (HOHA) Lactone by Retinal Pigmented Epithelial Cells

Metabolism of 4-Hydroxy-7-oxo-5-heptenoic Acid (HOHA) Lactone by Retinal Pigmented Epithelial Cells

The evolution of antiherbivore defenses and their contribution to species coexistence in the tropical tree genusInga

Gas-Liquid Chromatographic Isolation of Cytokinins from Natural Sources

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