23313-12-4Relevant articles and documents
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Lee at al.
, p. 127,131 (1978)
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AN IMPROVED SYNTHESIS OF L-ASCORBATE 2-POLYPHOSPHATE
Wang, Xiaoying,Qian, Wei-Wei,Seib, Paul A.
, p. 53 - 78 (2007/10/02)
L-Ascorbate (0) reacted rapidly with sodium trimetaphosphate (STMP) at 20-25 deg C and constant pH 9.5-10.0 in the presence of calcium ion.Barium and strontium ions also catalyzed the phosphorylation reaction, but not magnesium ion.The optimum reaction mixture was initially 1.4 M L-ascorbate, 1.8 M STMP, 1.7 M calcium hydroxide, and 0.4 M calcium chloride.Over a 20-min reaction period, pH was maintained by adding approximately 0.1 g calcium hydroxide in a 20percent aqueous slurry.The initial and final Ca/P ratios were ca. 0.36 and 0.42, respectively.The reaction products were 98.8percent 2-phosphorylated L-ascorbate, 1.2percent unreacted 0, and a trace of 4,5-ene, probably formed through 5,6-phosphorylated L-ascorbate 2-polyphosphate.High-performance liquid chromatography with UV detection and preparative anion-exchange chromatography showed the presence of eight 2-phosphorylated derivatives of 0 and two of the 4,5-ene skeleton.Rapid 2-phosphorylation prevented accumulation of the 4,5-elimination reaction, and three 5,6-cyclophosphoesters of 0 were found in the reaction products.A Ca/Na (3/1) salt of L-ascorbate 2-polyphosphate was isolated in 88percent yield as a white, odorless powder containing 33percent of L-ascorbate equivalents.Crystalline cyclohexylammonium salts of L-ascorbate 2-mono, di, and triphosphates were prepared.
X-Ray Analysis of L-Ascorbic Acid 2-O-Phosphate
Nomura, Hiroaki,Nakamichi, Hideo,Wada, Yoshikazu
, p. 1024 - 1029 (2007/10/02)
L-Ascorbic acid 2-O-phosphate,synthesized from 5,6-O-isopropylidene L-ascorbic acid by reaction with phosphoryl chloride in alkaline water-pyridine solution, crystallized as colorless plates of the dipiperazinium salt trihydrate, C6H9O9P*2C4H10N2*3H2O.Its molecular structure was determined by X-ray analisys.Keywords--Piperazinium L-ascorbic acid 2-O-phosphate; Magnesium L-ascorbic acid 2-O-phosphate; X-ray analysis; structure determination; CMR