InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m1/s1 |
COLNVLDHVKWLRT-MRVPVSSYSA-N |
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via phenylalanine )
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View more via ChEBI Ontology
(2R)-2-amino-3-phenylpropanoic acid
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D-phenylalanine
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D-alpha-Amino-beta-phenylpropionic acid
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KEGG COMPOUND
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D-Phe
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ChEBI
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D-PHENYLALANINE
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PDBeChem
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D-Phenylalanine
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KEGG COMPOUND
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DPN
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PDBeChem
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phenylalanine D-form
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ChemIDplus
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2804068
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Reaxys Registry Number
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Reaxys
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673-06-3
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CAS Registry Number
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KEGG COMPOUND
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673-06-3
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CAS Registry Number
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ChemIDplus
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83219
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Gmelin Registry Number
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Gmelin
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Singh V, Rai RK, Arora A, Sinha N, Thakur AK (2014) Therapeutic implication of L-phenylalanine aggregation mechanism and its modulation by D-phenylalanine in phenylketonuria. Scientific reports 4, 3875 [PubMed:24464217] [show Abstract] Self-assembly of phenylalanine is linked to amyloid formation toxicity in phenylketonuria disease. We are demonstrating that L-phenylalanine self-assembles to amyloid fibrils at varying experimental conditions and transforms to a gel state at saturated concentration. Biophysical methods including nuclear magnetic resonance, resistance by alpha-phenylglycine to fibril formation and preference of protected phenylalanine to self-assemble show that this behaviour of L-phenylalanine is governed mainly by hydrophobic interactions. Interestingly, D-phenylalanine arrests the fibre formation by L-phenylalanine and gives rise to flakes. These flakes do not propagate further and prevent fibre formation by L-phenylalanine. This suggests the use of D-phenylalanine as modulator of L-phenylalanine amyloid formation and may qualify as a therapeutic molecule in phenylketonuria. | Matsunaga I, Komori T, Mori N, Sugita M (2012) Identification of a novel tetrapeptide structure of the Mycobacterium avium glycopeptidolipid that functions as a specific target for the host antibody response. Biochemical and biophysical research communications 419, 687-691 [PubMed:22382026] [show Abstract] Mycobacterium avium complex (MAC) is a group of non-tuberculous mycobacteria that cause tuberculosis-like diseases in humans. Unlike Mycobacterium tuberculosis, MAC expresses high levels of glycopeptidolipids (GPLs) containing a well-defined tetrapeptide-amino alcohol core, composed of D-phenylalanine, D-allo-threonine, D-alanine, and L-alaninol, that is modified with a fatty acid and sugar residues. Surprisingly, however, a careful scrutiny of the mass spectrum of MAC GPLs revealed the presence of ions that could not readily accountable for the known GPL structure. The magnitude of the ions was increased prominently when GPLs were isolated from the valine-supplemented culture, and the ions representing the authentic GPL species were diminished, suggesting the possibility that the basic structure of the peptide backbone might be altered in response to the exogenously added valine. Indeed, further mass spectrometry (MS)/MS and gas chromatography-MS analysis indicated a substitution of D-valine for the N-terminal D-phenylalanine of the tetrapeptide core, and the presence of D-valine and the absence of D-phenylalanine was confirmed by high-performance liquid chromatography, using the derivatized amino acid residues that were released from the tetrapeptide. Finally, specific antibodies to the purified valine-containing GPL species were detected in the serum of a MAC-infected guinea pig. Therefore, these results identify a new molecular species of MAC GPLs with immunogenic potential. | Jukić T, Rojc B, Boben-Bardutzky D, Hafner M, Ihan A (2011) The use of a food supplementation with D-phenylalanine, L-glutamine and L-5-hydroxytriptophan in the alleviation of alcohol withdrawal symptoms. Collegium antropologicum 35, 1225-1230 [PubMed:22397264] [show Abstract] We described the use of a food supplementation with D-phenylalanine, L-glutamine and L-5-hydroxytriptophan in the alleviation of alcohol withdrawal symptoms in patients starting a detoxification therapy. Since abstinence from ethanol causes a hypodopaminergic and a hypoopioidergic environment in the reword system circuits, manifesting with withdrawal symptoms, food supplements that contains D-phenylalanine a peptidase inhibitor (of opioide inactivation) and L-amino-acids (for dopamine synthesis) were used to replenish a lack in neurotransmitters and alleviate the symptoms of alcohol withdrawal. 20 patients suffering from alcohol addictions starting a detoxification therapy have been included in a prospective, randomized, double blind study. The patients have been randomly devided in two groups. One group recieved for a period of 40 days a food supplement containing D-phenylalanine, L-glutamine and L-5-hydroxytriptophan (investigation group), and the control (placebo) group. On the first day of hospitalization the patients performed a SCL-90-R test, and blood samples were taken for measuring liver enzymes, total bilirubin, unbound cortisol and lymphocyte populations. The same was done on the 40th day of hospitalization. During the therapy a significant decrease in SCL-90-R psychiatric symptoms scores and a significant increase in CD4 lymphocyte count was observed in the investigation group. The cortisol values were significantly, but equally decreased in both groups, the same was with the liver enzymes and the total bilirubin values. We conclude that abstinence causes a major stress for the patients. The use of food supplement containing D-phenylalanine, L-glutamine and L-5-hydroxytriptophan alleviates the withdrawal symptoms and causes a rise in CD4 lymphocyte population, but it dose not affect the serum cortisol levels, which are probably more affected by liver inflammation and the liver restitution. | Donzelle G, Bernard L, Deumier R, Lacome M, Barre M, Lanier M, Mourtada MB (1981) [Curing trial of complicated oncologic pain by D-phenylalanine (author's transl)]. Anesthesie, analgesie, reanimation 38, 655-658 [PubMed:7114516] [show Abstract]
UnlabelledAim of investigations: Very often, chronic pain treatments used for the management of terminal ill cancer patients do not prevent acute or incident pain from coming up. For twenty months D-phenylalanine (DPA), an enkephalinase inhibitor, has been investigated in order to forestall this pain.MethodsNine caucasian patients, three males and six females, between forty-nine and seventy-eight, were selected for this trial after informed consent. They were all undergoing severe incident pains related to complications (scabies, osteoporosis, painful cough or colic, Charley-Horse, RX-necrosis of skin or mucous membranes, etc) in spite of having their chronic pain component cured: phanol-rhizotomy: two cases, neuro-adrenolysis by alcohol: four cases, Brampton mixture: three cases. They were administered DPA, 250 mg three times a day for fifteen days, followed by a ten days pause, resumption and so on.ResultsSeven patients out of nine were alleviated and they never claimed for more or other analgesics until they died. Four of them got very good ataraxia during the same time (survival mean x = 99,33 days). No side effect was reported, even in patients taking Brampton mixture.ConclusionsDPA seems a useful drug to prevent acute or incident pain in malignant diseases. Our data point out the consequences the enkephalinases inhibitors will take up for the cure of intractable cancer pain. |
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