77479-02-8Relevant articles and documents
Reaction of acetaldehyde with 5-aminolevulinic acid via dihydropyrazine derivative
Suzuki, Toshinori,Yasuhara, Naoki,Ueda, Takashi,Inukai, Michiyo,Mio, Mitsunobu
, p. 126 - 129 (2015)
When a solution of 5-aminolevulinic acid (ALA) was incubated with acetaldehyde at neutral pH, a product was generated. This product was identified as 3-ethylpyrazine-2,5-dipropanoic acid (ETPY). ETPY was stable at neutral pH. It has been reported that ALA dimerizes at neutral pH generating 3,6-dihydro-pyrazine-2,5-dipropanoic acid (DHPY), and subsequently resulting in pyrazine-2,5-dipropanoic acid (PY) by autoxidation. In the present reaction, DHPY generated from ALA reacted with acetaldehyde, resulting in ETPY. Preadministration of ALA 3 min prior to acetaldehyde injection supressed the toxicity of acetaldehyde in male mice. These results suggest that ALA may be useful as a scavenger for acetaldehyde.
The Forgotten Pyrazines: Exploring the Dakin–West Reaction
Würdemann, Martien A.,Ni?u, Cristina,De Wildeman, Stefaan M. A.,Bernaerts, Katrien V.,Orru, Romano V. A.
supporting information, p. 8090 - 8100 (2020/06/09)
Pyrazines are an underreported class of N-heterocycles available from nitrogen-rich biomass presenting an interesting functional alternative for current aromatics. In this work, access to pyrazines obtained from amino acids by using the 90 year old Dakin–West reaction was explored. After a qualitative screening several functional proteinogenic amino acids proved good substrates for this reaction, which were successfully scaled to multigram scale synthesis of the corresponding intermediate α-acetamido ketones. Subsequently, the conditions towards pyrazine formation using δ-amino-levulinic acid were optimized, and these were employed to synthesize a relevant set of five functional dimethylpyrazines in high purity. These pyrazines can be considered a versatile toolbox of aromatic building blocks for a wide range of applications, such as in the synthesis of polymers or metal–organic frameworks.
PYRAZINE-2,5-DIPROPIONIC ACID MONOESTER AND PRODUCTION METHOD THEREOF
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Paragraph 0026, (2018/11/22)
PROBLEM TO BE SOLVED: To provide stable pyrazine-2,5-dipropionic acid derivatives. SOLUTION: Pyrazine-2,5-dipropionic acid monoalkyl esters and their production method are provided. COPYRIGHT: (C)2016,JPO&INPIT
NOVEL CRYSTAL OF 5-AMINOLEVULINIC ACID PHOSPHATE AND PROCESS FOR PRODUCTION THEREOF
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Page/Page column 11, (2009/06/27)
To provide a novel crystal of 5-aminolevulinic acid phosphate having a high thermal stability, a high melting point, and an excellent moisture absorption resistance as well as a process for producing the same. A crystal of 5-aminolevulinic acid phosphate, which shows characteristic peaks at 7.9° ±0.2°, 15.8° ±0.2°, 18.9° ±0.2°, 20.7° ±0.2°, 21.1° ±0.2°, 21.4° ±0.2°, 22.9° ±0.2°, 33.1° ±0.2°, and 34.8 ±0.2° as diffraction angles 2θ in a powder X-ray diffraction, and a process for producing the same.
Degradation mechanism and stability of 5-aminolevulinic acid
Bunke,Zerbe,Schmid,Burmeister,Merkle,Gander
, p. 1335 - 1341 (2007/10/03)
The physiological substance and precursor of the heme synthesis 5-aminolevulinic acid (ALA) is a promising prodrug for photodiagnosis and photodynamic therapy of epithelial tumors, particularly in urological and gynecological tissues. For the clinical use of this substance, a chemically stable and sterile drug formulation is required. In the present study, degradation mechanism of ALA in aqueous solution and possibilities to improve its stability were examined. A capillary electrophoretic method was developed that was suitable for the quantification of ALA and of two degradation products. The intermediate degradation product was 2,5-dicarboxyethyl-3,6-dihydropyrazine, which was further oxidized to 2,5-dicarboxyethylpyrazine. The structures of the degradation products were proven by 1H and 13C nuclear magnetic resonance spectroscopy. ALA degradation was very efficiently inhibited by adjusting the pH of the aqueous solution to a value 5 and by purging with nitrogen. Additives such as antioxidants did not improve the ALA stability. These results demonstrated that low pH ALA aqueous solution may be one possible dosage form to be considered for market introduction. (C) 2000 Wiley-Liss, Inc.
The nonenzymatic cyclic dimerisation of 5-aminolevulinic acid
Butler,George
, p. 7879 - 7886 (2007/10/02)
The nonenzymatic cyclic dimerisation of 5-aminolevulinic aid (5-ALA) leads to the formation of a pyrazine (3) and, under some circumstances, pseudo-porphobilinogen (1). On the other hand, the enzyme-catalysed process leads to porphobilinogen (PBG). The products of the former reaction were identified from their NMR spectra and mechanisms for their formation are proposed.
CONDENSATION PRODUCTS OF THE PORPHYRIN PRECURSOR 5-AMINOLEVULINIC ACID
Franck, Burchard,Stratmann, Helmut
, p. 919 - 923 (2007/10/02)
Condensation of the biogenetic porphyrin precursor 5-aminolevulinic acid (1) in alkaline solution yields besides some porphobilinogen (2) a dihydropyrazine (6) as the predominant product, which was isolated and characterized after dehydrogenation to the stable pyrazine (7a).This ends a longstanding uncertainty and reveals that the azomethine reaction, as can be expected for α-aminoketones, is strongly preferred by 5-aminolevulinic acid (1) under nonenzymatic conditions.A nor-porphobilinogen (9) was formed by condensation of a protected aminoacetoacetic ester with (1).
