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N-(Tetr-Butoxycarbonyl)-L-Se-Methylselenocysteine置于三氟乙酸体系中,用 二氯甲烷 用作溶剂,化学反应 0.42H,以100%的收率获得3-(甲基硒基)-L-丙氨酸
参考文献:A Method Of Using Synthetic L-Se-Methylselenocysteine As A Nutriceutical And A Method Of Its Synthesis
标题:A Method Of Using Synthetic L-Se-Methylselenocysteine As A Nutriceutical And A Method Of Its Synthesis
摘要:描述了一种合成和使用l-Se-甲硒氨酸作为一种营养保健品,基于l-Se-甲硒氨酸对正常细胞比l-硒蛋氨酸毒性较小的知识.合成过程包括将n-(叔丁氧羰基)-L-丝氨酸与二烷基重氮二羧酸酯和三烷基膦,三芳基膦和磷酸酯中的至少一种混合,形成包含n-(叔丁氧羰基)-L-丝氨酸β-内酯的第一混合物.甲硒醇或其盐与n-(叔丁氧羰基)-L-丝氨酸β-内酯混合,形成包含n-(叔丁氧羰基)-Se-甲硒氨酸的第二混合物.将n-(叔丁氧羰基)-Se-甲硒氨酸中的叔丁氧羰基团去除,形成l-Se-甲硒氨酸.这种合成显著改善了这种天然存在的稀有有机硒形式的可制造性,制造效率和实用性.例如,以这种方式形成的l-Se-甲硒氨酸可用作一种营养保健品,添加到人类或动物的饮食中,以达到各种有益目的,例如预防或减少患癌症的风险.

专利信息

专利号:US-2007088086-A1
优先权日:1999-08-16
标题 :Method of using synthetic L-Se-methylselenocysteine as a nutriceutical and a method of its synthesis
发明人：SPALLHOLZ JULIAN E; REID TED W; WALKUP ROBERT D
权利人:PHARMASE INC
摘要:A synthesis of and use for L-Se-methylselenocysteine as a nutriceutical is described, based upon the knowledge that L-Se-methylselenocysteine is less toxic than L-selenomethionine towards normal cells. The synthesis proceeds by mixing N-(tert-butoxycarbonyl)-L-serine with a dialkyl diazodicarboxylate and at least one of a trialkylphosphine, triarylphosphine, and phosphite to form a first mixture that includes N-(tert-butoxycarbonyl)-L-serine β-lactone. Methyl selenol or its salt is mixed with the N-(tert-butoxycarbonyl)-L-serine β-lactone to form a second mixture that includes N-(tert-butoxycarbonyl)-Se-methylselenocysteine. The tert-butoxycarbonyl group is removed from the N-(tert-butoxycarbonyl)-Se-methylselenocysteine to form L-Se-methylselenocysteine. This synthesis significantly improves the manufacturability, manufacturing efficiency, and utility of this naturally occurring rare form of organic-selenium. L-Se-methylselenocysteine formed, for example, in this manner may be used as a nutriceutical for supplementation into the diets of humans or animals for various beneficial purposes, such as, for example, to prevent or reduce the risk of developing cancer.

专利号:EP-1205471-A1
优先权日:2000-10-02
标题:A method of using synthetic L-SE-Methylselenocysteine as a nutriceutical and a method of its synthesis
发明人：SPALLHOLZ JULIAN E; REID TED W; WALKUP ROBERT D
权利人:PHARMASE INC
摘要:A synthesis of and use of L-Se-methylselenocysteine as a nutriceutical isndescribed, based upon the knowledge that L-Se-methylselenocysteine is lessntoxic than L-selenomethionine towards normal cells. The synthesis proceedsnby mixing N-(tert-butoxycarbonyl)-L-serine with a dialkyl diazodicarboxylatenand at least one of a trialkylphosphine, triarylphosphine and phosphite to formna first mixture that includes N-(tert-butoxycarbonyl)-L-serine β-lactone.nMethyl selenol or its salt is mixed with the N-(tert-butoxycarbonyl)-L-serine β-lactonento form a second mixture that includes N-(tert-butoxycarbonyl)-Se-methylselenocysteine.nThe text butoxycarbonyl group is removed from the N-(tert-butoxycarbonyl)-Se-methylselenocysteinento form L-Se-methylselenocysteine.nThis synthesis significantly improves thenmanufacturability, manufacturing efficiency and utility of this naturallynoccurring rare form of organic-selenium. L-Se-methylselenocysteine formed,nfor example, in this manner may be used as a nutriceutical for supplementationninto the diets of humans or animals for various beneficial purposes, such as, fornexample, to prevent or reduce the risk of developing cancer.

专利号:US-8193156-B1
优先权日:2006-05-18
标 题:Dipeptides incorporating selenoamino acids with enhanced bioavailability—synthesis, pharmaceutical and cosmeceutical applications thereof
发明人：MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; CHANDRAMOULI RENUKESHWAR H
权利人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; CHANDRAMOULI RENUKESHWAR H; SAMI LABS LTD
摘要:Disclosed is a novel synthetic method for isomeric peptides through an appropriate linkage of L-selenomethionine or Se-Methyl-L-selenocysteine with L-glutamic acid. The novel synthetic method produces isomeric peptides of L-selenomethionine or Se-Methyl-L-selenocysteine that exhibit (i) enhanced water solubility; (ii) enhanced rate of dissolution in water; (iii) enhanced bioavailability; (iv) excellent vascular endothelial growth factor promoting activity; (v) excellent anti-5-alpha-reductase activity; (vi) capabilities to prevent/reduce “hair fallâ€? and promote “hair growthâ€?, thereby maintaining a perfect homeostasis for “hair careâ€?. Cosmeceutical and pharmaceutical compositions comprising the isomeric peptides obtained through an appropriate linkage of L-selenomethionine or Se-Methyl-L-selenocysteine with L-glutamic acid are also disclosed. Other dipeptides with several other amino acids and uses thereof are also disclosed.

专利号:CN-117586293-A
优先权日:2024-01-11
标题:A new type of organic selenium and boron reagent and its application in the synthesis of L-selenium-methylselenocysteine

专利号:CN-218854305-U
优先权日:2022-12-09
标题 :A kind of stirring device for synthesis of L-selenium-methylselenocysteine

专利号:CN-117586293-B
优先权日:2024-01-11
标 题 :Novel organic selenium boron reagent and application thereof in synthesis of L-selenium-methyl selenocysteine