184955-21-3Relevant articles and documents
Plant phenolics affect oxidation of tryptophan
Salminen, Hanna,Heinonen, Marina
, p. 7472 - 7481 (2008)
The effect of berry phenolics such as anthocyanins, ellagitannins, and proanthocyanidins from raspberry (Rubus idaeus), black currant (Ribes nigrum), and cranberry (Vaccinium oxycoccus) and byproducts of deoiling processes rich in phenolics such as rapese
Mass spectrometric analysis of oxidized tryptophan
Van de Weert, Marco,Lagerwerf, Fija M.,Haverkamp, Johan,Heerma, Wigger
, p. 884 - 891 (1998)
Oxindolylalanine and oxindolylalanine-containing peptides were prepared by treatment of tryptophan and tryptophan-containing peptides with mixtures of dimethyl sulfoxide and hydrochloric acid in acetic acid (DMSO-HCl-HAc). The reaction between tryptophan and DMSO-HCl-HAc was monitored by fast atom bombardment mass spectrometry (FAB-MS) and the proposed chlorotryptophan intermediate in the reaction was observed. Almost complete conversion of tryptophan to oxindolylalanine was obtained in reaction mixtures containing 3.75 M HCl when the reaction was performed in an open tube. A higher HCl concentration (5.5 M) and a closed reaction tube promoted the formation of by-products, such as dioxindolylalanine and 3-chlorooxindolylalanine. Extensive hydrolysis C-terminal of tryptophan was observed when tryptophan-containing peptides were treated with DMSO-HCl-HAc containing 5.5 M HCl, during which the tryptophan residue was modified to dioxindolylalanine lactone. Hydrolysis was not observed in mixtures containing 3.75 M HCl. The presence of oxindolylalanine in peptides could be demonstrated by characteristic peaks in FAB collision-induced dissociation tandem mass spectra.
The Halicylindramides, Farnesoid X Receptor Antagonizing Depsipeptides from a Petrosia sp. Marine Sponge Collected in Korea
Hahn, Dongyup,Kim, Hiyoung,Yang, Inho,Chin, Jungwook,Hwang, Hoosang,Won, Dong Hwan,Lee, Byoungchan,Nam, Sang-Jip,Ekins, Merrick,Choi, Hyukjae,Kang, Heonjoong
, p. 499 - 506 (2016/04/19)
Three new structurally related depsipeptides, halicylindramides F-H (1-3), and two known halicylindramides were isolated from a Petrosia sp. marine sponge collected off the shore of Youngdeok-Gun, East Sea, Republic of Korea. Their planar structures were elucidated by extensive spectroscopic data analyses including 1D and 2D NMR data as well as MS data. The absolute configurations of halicylindramides F-H (1-3) were determined by Marfey's method in combination with Edman degradation. The absolute configurations at C-4 of the dioxyindolyl alanine (Dioia) residues of halicylindramides G (2) and H (3) were determined as 4S and 4R, respectively, based on ECD spectroscopy. The C-2 configurations of Dioia in 2 and 3 were speculated to both be 2R based on the shared biogenesis of the halicylindramides. Halicylindramides F (1), A (4), and C (5) showed human farnesoid X receptor (hFXR) antagonistic activities, but did not bind directly to hFXR.
Synthesis of peptides containing 5-hydroxytryptophan, oxindolylalanine, N-formylkynurenine and kynurenine
Todorovski, Toni,Fedorova, Maria,Hennig, Lothar,Hoffmann, Ralf
scheme or table, p. 256 - 262 (2012/01/13)
ROS, continuously produced in cells, can reversibly or irreversibly oxidize proteins, lipids, and DNA. At the protein level, cysteine, methionine, tryptophan, and tyrosine residues are particularly prone to oxidation. Here, we describe the solid phase synthesis of peptides containing four different oxidation products of tryptophan residues that can be formed by oxidation in proteins in vitro and in vivo: 5-HTP, Oia, Kyn, and NFK. First, we synthesized Oia and NFK by selective oxidation of tryptophan and then protected the ${bf alpha}$-amino group of both amino acids, and the commercially available 5-HTP, with Fmoc-succinimide. High yields of Fmoc-Kyn were obtained by acid hydrolysis of Fmoc-NFK. All four Fmoc derivatives were successfully incorporated, at high yields, into three different peptide sequences from skeletal muscle actin, creatin kinase (M-type), and ${bf beta}$-enolase. The correct structure of all modified peptides was confirmed by tandem mass spectrometry. Interestingly, isobaric peptides containing 5-HTP and Oia were always well separated in an acetonitrile gradient with TFA as the ion-pair reagent on a C18-phase. Such synthetic peptides should prove useful in future studies to distinguish isobaric oxidation products of tryptophan.
Reaction du L-tryptophane avec le radical peroxyle du trichlorocarbone (CCl3OO*) et l'oxygene singulet (1O2): formation des differentes paires d'hydroperoxydes isomeriques
Langlois, R.,Ali, H.,Lier, J. E. van
, p. 985 - 1000 (2007/10/02)
Radiolytic formation of the trichloromethylperoxy radical, in an oxygenated aqueous solution containing L-tryptophan, results in the formation of two new hydroperoxides which were identified as the epimeric hydroperoxyoxindolylalanines 6 and 7.These peroxides are suggested to be formed via addition of the CCl3OO* radical onto the C(2) of the indole ring followed by addition of molecular oxygen onto the resulting carbon centered radical and subsequent decomposition of the trichloromethylperoxy adduct.Thermal decomposition of the primary hydroperoxides 6 and 7gives a series of known L-tryptophan degradation products including N-formylkynurenine (10), L-kynurenine (9), and the corresponding epimeric alcohols 5 and 8.Trichloromethylperoxy addition onto the C(2) or C(3) of L-tryptophan following rearrangement to yield an intermediate 2,3-epoxide derivative, may explain the formation of oxindolylalanine (11) and the epimeric hydroxypyrroloindoles 1 and 3 via epoxide hydrolysis.The hydroperoxides 6 and 7 are distinctly different from those observed upon singlet oxygen oxidation of L-tryptophan and together with their degradation and rearrangement products, these hydroperoxides could serve as probes to study mechanisms of the oxidative degradation of proteins.
Preparative Separation of the Diastereomers of Dioxindolyl-L-alanine and Assignment of Stereochemistry at C-3
Labroo, Rita B.,Cohen, Louis A.
, p. 4901 - 4904 (2007/10/02)
The diastereomers of dioxindolyl-L-alanine are obtained in a 1:1 ratio by air oxidation of oxindolyl-L-alanine.Preparative separation of the diastereomers is achieved by reverse-phase HPLC.Stereochemistry of the hydroxyl group at C-3 is assigned by transformation to a related pair of diastereomers of known stereochemistry.
