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Marfey

Marcus equation Marezine Marfey s reagent Margaric acid [506-12-7]... [Pg.595]

Fig. 7-6). Two unichiral amides which have been known capable of this reaction are 1-phenylethylamine [15] and l-(l-naphthyl)ethylamine [16]. Marfey s reagent [N-a-(2,4-dinitro-5-fluorophenyl)-L-alaninamide] was introduced as a reagent to deriva-tize amino acids with cyclopentane, tetrahydroisoquinoline or tetraline structures [17]. Simple chiral alcohols such as 2-octanol can also be used to derivatize acids such as 2-chloro-3-phenylmethoxypropionic acid [18]. [Pg.190]

A simple and rapid method of separating optical isomers of amino acids on a reversed-phase plate, without using impregnated plates or a chiral mobile phase, was described by Nagata et al. [27]. Amino acids were derivatized with /-fluoro-2,4-dinitrophenyl-5-L-alanine amide (FDAA or Marfey s reagent). Each FDAA amino acid can be separated from the others by two-dimensional elution. Separation of L- and D-serine was achieved with 30% of acetonitrile solvent. The enantiomers of threonine, proline, and alanine were separated with 35% of acetonitrile solvent and those of methionine, valine, phenylalanine, and leucine with 40% of acetonitrile solvent. The spots were scraped off the plate after the... [Pg.211]

Marfey, S.P., and Tsai, K.H. (1975) Cross-linking of phospholipids in human erythrocyte membrane. Biochem. Biophys. Res. Comm. 65, 31-38. [Pg.1091]

P Marfey. Determination of D-amino acids, n. Use of a bifunctional reagent 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res Commun 49, 591, 1984. [Pg.124]

JG Adamson, T Hoang, A Crivici, GA Lajoie. Use of Marfey s reagent to quantitate racemization upon anchoring of amino acids to solid supports for peptide synthesis. Anal Biochem 202, 210, 1992. [Pg.152]

The enantiomeric purity of protected amino acids used in peptide synthesis can be determined by pre-column partial deprotection followed by derivatization with Marfey s reagent (116). The Marfey diastereoisomers can be easily resolved and determined by RP-HPLC using an ODS-Hypersil column288. Fifteen amino acids collected from mammalian tissues were derivatized with Marfey s reagent and subjected to two-dimensional TLC. Each individual spot (enantiomeric mixture of a diasteroisomer) was then resolved by RP-HPLC. Except for tyrosine (46) and histidine (117), subnanomole quantities of enantiomers could be analyzed289,290. [Pg.1089]

Direct and indirect chromatographic methods were developed and compared in systematic examinations for the enantioseparation of P-amino acids direct separation of underivatized analytes involved the use of commercially available Crownpak CR(-I-), teicoplanin, and ristocetin A CSPs [148], while indirect separation was based on precolumn derivatization with 2,3,4,6-tetra-G-acetyl-f)-D-glucopyranosyl isothiocyanate (GITC) or A - a-(2,4-dinitro-5-fluorophenyl)-L-alaninamide (EDAA, Marfey s reagent), with subsequent separation on a nonenantioselective column. [Pg.141]

CE has been applied extensively for the separation of chiral compounds in chemical and pharmaceutical analysis.First chiral separations were reported by Gozel et al. who separated the enantiomers of some dansylated amino acids by using diastereomeric complex formation with Cu " -aspartame. Later, Tran et al. demonstrated that such a separation was also possible by derivatization of amino acids with L-Marfey s reagent. Nishi et al. were able to separate some chiral pharmaceutical compounds by using bile salts as chiral selectors and as micellar surfactants. However, it was not until Fanali first showed the utilization of cyclodextrins as chiral selectors that a boom in the number of applications was noted. Cyclodextrins are added to the buffer electrolyte and a chiral recognition may... [Pg.37]

A (SCA) HMP (TFA) c[-Trp-Ile-Val-D-Pro-Asp-] and other peptides containing Asp at the C-terminus BOP/HOBt FAB-MS, Marfey s test for racemiza-tion racemization of Asp is minimized by using only equiv DIPEA [3691... [Pg.490]

L. patella from Fiji contained patellins 1-5 (50-54) [82] and earlier, solution- and solid-state conformational studies were carried out on patellin 2 (51), and the structure was determined by X-ray analysis [83]. A Lissoclinum sp. from the Great Barrier Reef yielded patellins 3 (52), 5 (54) and 6 (55) and the heptapeptide trunkamide A (56) [82]. Compounds 50-56 were all identified by interpretation of spectral data and through use of Marfey s method to determine the absolute stereochemistry of the constituent amino acids [82]. A total synthesis of the proposed structure of trunkamide A (56) revealed that the structure... [Pg.628]

A Palauan species of Dysidea contained 15-acetylthioxyfurodysinin lactone (327), that binds to human leukotriene B4 (LTB4) receptor. The structure was determined by spectral data analysis and confirmed by synthesis involving photo-oxidation of 15-acetylthioxyfurodysinin (328), which co-occurs with it in the sponge [297,298]. An Australian species of Euryspongia also contained 15-acetylthioxyfurodysin (329) and 15-acetylthioxyfurodysinin (328) [299]. A sample of D. herbacea from the Great Barrier Reef contained (-)-neodysidenin (330) and the absolute configuration was determined by capillary electrophoresis of Marfey s derivatives [300]. [Pg.667]

An alternative solid-phase synthesis of peptide thioamides that uses methyl dithioesters to introduce the sulfur involves addition of DMAP and cesium trifluoroacetate. 24 These additives greatly accelerate the thioamide-forming reaction and give low levels of racemi-zation according to Marfey s test analysis 25 of an Alaip[C(=S)—NH]Val product. [Pg.460]

Thiazole-containing linear peptides have also been isolated from tunicates. Virenamides A-E (412-416) were obtained from the didemnid tunicate Diplosoma virens, which contains symbiotic prokaryotic algae in its cloacal cavity. The structures of virenamides A-C were determined by HPLC analysis using Marfey s procedure [323] while the absolute stereochemistry of virenamide E (416) was proven by its synthesis from virenamide A (412) [324], Compounds 412-416 showed modest cytotoxicity toward a panel of cultured cells and 412 also exhibited topoisomerase II inhibitory activity. [Pg.888]


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See also in sourсe #XX -- [ Pg.260 ]

See also in sourсe #XX -- [ Pg.317 , Pg.388 , Pg.392 ]




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Marfey analysis

Marfey’s reagent

Reagents Marfey

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