Synthesis and pilot-scale process of L-selenium-methylselenocysteine

被引:0
|
作者
Liao J. [1 ]
Yang P. [1 ]
Li Y. [1 ]
Liu J. [1 ]
Dai Y. [1 ]
Zheng J. [1 ]
Ou S. [1 ]
Zhou H. [1 ]
机构
[1] Department of Food Science and Engineering, Jinan University, Guangzhou
关键词
L-selenium-methylselenocysteine; L-selenocystine; reaction kinetics; reduction; synthesis;
D O I
10.3969/j.issn.1003-9015.2023.06.010
中图分类号
学科分类号
摘要
The synthesis of L-selenium-methylselenocysteine (L-SeMC) has problems of low safety factor and high cost of post-treatment. A new synthetic method was proposed in this study. Optimized process conditions were first obtained in laboratory, and then a pilot production line was designed and built to verify the process stability. The laboratory results show that L-serine is chlorinated to obtain 3-chloro-L-alanine hydrochloride (yield: 89.7%), and then reacts with sodium diselenide by sodium triacetoxyborohydride reduction to generate L-selenocystine(L-SeC2) (yield: 73.0%). The target product is finally obtained by reduction and methylation under the molar ratio of n(L-SeC2):n(iodomethane):n(sodium triacetoxyborohydride) =1.00:4.02:1.58 (yield:78.3%). The yields of the pilot production line are close to or higher than that of the laboratorial results, which helps for the industrial production of L-SeMC. © 2023 Zhejiang University. All rights reserved.
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页码:951 / 961
页数:10
相关论文
共 34 条
  • [1] KIELISZEK M., Selenium-fascinating microelement, properties and sources in food, Molecules, 24, 7, (2019)
  • [2] RAYMAN M P., Selenium intake, status, and health: A complex relationship, Hormones, 19, 1, pp. 9-14, (2020)
  • [3] National food safety standard—Food nutrition enhancer—L-selenium-methylselenocysteine: GB 1903.12−2015, (2016)
  • [4] KIM D, KU B, CHOI E M., Se-methylselenocysteine stimulates migration and antioxidant response in HaCaT keratinocytes: Implications for wound healing, Journal of Trace Elements in Medicine and Biology, 58, (2020)
  • [5] DU X B, SHI Q Q, ZHAO Y X, Et al., Se-methylselenocysteine (SMC) improves cognitive deficits by attenuating synaptic and metabolic abnormalities in Alzheimer's mice model: A proteomic study, ACS Chemical Neuroscience, 12, 7, pp. 1112-1132, (2021)
  • [6] XIE Y L, LIU Q, ZHENG L, Et al., Se-methylselenocysteine ameliorates neuropathology and cognitive deficits by attenuating oxidative stress and metal dyshomeostasis in Alzheimer model mice, Molecular Nutrition & Food Research, 62, 12, (2018)
  • [7] MA J, HUANG J, SUN J L, Et al., L-Se-methylselenocysteine sensitizes lung carcinoma to chemotherapy, Cell Proliferation, 54, 5, (2021)
  • [8] LENDVAI G, SZEKERCZES T, KONTSEK E, Et al., The effect of methylselenocysteine and sodium selenite treatment on microRNA expression in liver cancer cell lines, Pathology & Oncology Research, 26, 4, pp. 2669-2681, (2020)
  • [9] HU T, LI H F, ZHAO G S, Et al., Selenium enriched Hypsizygus marmoreus, a potential food supplement with improved Se bioavailability, LWT, 140, (2021)
  • [10] DE OLIVEIRA A P, NAOZUKA J, LANDERO-FIGUEROA J A., Effects of Se(IV) or Se(VI) enrichment on proteins and protein-bound Se distribution and Se bioaccessibility in oyster mushrooms, Food Chemistry, 383, (2022)