CAS: 98541-64-1; Tert-Butyl (S)-(2-Oxooxetan-3-yl)Carbamate

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CAS号3262-72-4 B°C-L-丝氨酸 | CAS号24424-99-5 二碳酸二叔丁酯 | CAS号61925-78-8 N-B°C-S-4-甲基苄基-... | CAS号55477-80-0 2-叔丁氧羰基氨基丙烯酸甲酯 | CAS号73259-81-1 N(α)-B°C-L-2,3-二氨丙酸 | CAS号76387-70-7 N(α)-B°C-D-2,3-二氨基丙酸 | CAS号102830-49-9 B°C-S-苄基-D-半胱氨酸 | CAS号138775-03-8 (S)-4-((苄氧羰基)羰基... | CAS号112839-95-9 (S)-3-氨基氧杂环丁-2-... | CAS号138423-86-6 (S)-1-叔丁基2-甲基4,... | CAS号348081-42-5 (R)-2-TERT-BUTO...

Boc-L-丝氨酸置于丁炔二酸二甲酯体系中,用 四氢呋喃 作为反应溶剂,化学反应 2.33H,反应生成 (S)-α-Boc-氨基-β-丙内酯
参考文献:Interactive Design And Synthesis Of A Novel Antibacterial Agent
标题:Interactive Design And Synthesis Of A Novel Antibacterial Agent
摘要:β-内酰胺化合物通过酰化活性位点丝氨酸的羟基作用于青霉素识别酶.当产生的酰酶在动力学上是稳定的,如青霉素结合蛋白(pbp)的情况下,细菌细胞壁的生物合成被抑制,导致生物体的死亡.如果能确定青霉素结合蛋白的三维结构要求(即平衡的适合性)和催化(即反应性)步骤的需求,可能会实现针对pbp的抗菌剂的全新设计.对来自链霉菌r61的pbp的活性位点模型,使用分子力学计算处理"适合性",并使用从头算分子轨道计算处理"反应性",得出一个想法,即抗生素的羧基(g1)和酰胺n-H(g2)与酶-底物复合物中的赖氨酸氨基团和缬氨酸羰基团形成氢键.这两个氢键将丝氨酸羟基置于抗生素的凸面上,处于通过中性反应由水催化的直接质子转移至β-内酰胺氮原子的位置.与这种机制相关的结构-反应关系的分子轨道计算表明,C=n与β-内酰胺n-C(=o)是生物等同物,与醇类反应时与β-内酰胺相当,产物ro(C-N)H基本上是不可逆的(−δe > 10 Kcal/mol).因此,含有由c=n分隔的g1和g2的结构,并以不同方式相对于这个功能团定位的结构已经通过计算合成并检验其适合于pbp模型的能力.这种策略确定了一个被羟基和羧基取代的2H-5,6-二氢-1,4-噻嗪作为化学合成的目标.然而,探索性实验表明,该化合物的c=n与内环和外环烯胺互变异构体平衡.这要求对c2位置进行取代,并且羟基不能连接到邻近c=n的碳原子.这些条件在2,2-二甲基-3-(2-羟基丙基)-1,4-噻嗪中得到满足,该化合物还展现出与pbp模型的必要适合性.这种化合物的两个对映体已经从d-丝氨酸和l-丝氨酸合成.从l-丝氨酸衍生的化合物不活跃.从d-丝氨酸衍生的化合物表现出抗菌活性,但不稳定,并且尚未进行与pbp的结合研究.希望如果引物结构的修改导致具有改善化学稳定性的化合物,这些研究可以进行.
DOI:10.1139/v94-133

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-5200526-A
优先权日:1987-04-27
标题:Syntheses of optically pure α-amino acids from 3-amino-2-oxetanone salts
发明人：ARNOLD LEE D; VEDERAS JOHN C
权利人:UNIV ALBERTA
摘要:A process for the preparation of optically pure α-amino acids comprising the nucleophilic ring-opening of 3-amino-2-oxetanone salts. N-Protected serine β-lactones are deprotected to form heretofore unknown 3-amino-2-oxetanone and its corresponding salts. In turn these previously unknown 3-amino-2-oxetanone salts may be used in the synthesis of other novel or rare stereochemically-pure free amino acids.

专利号:US-5846993-A
优先权日:1992-12-22
标题:HIV protease inhibitors
发明人：DRESSMAN BRUCE A; FRITZ JAMES E; KALDOR STEPHEN W; KALISH VINCENT J; REICH SIEGFRIED HEINZ; TATLOCK JOHN H; RODRIGUEZ MICHAEL J
权利人:AGOURON PHARMA
摘要:HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optionally other anti-viral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.

专利号:US-6271235-B1
优先权日:1992-12-22
标题:HIV protease inhibitors
发明人：DRESSMAN BRUCE A; FRITZ JAMES E; KALDOR STEPHEN W; KALISH VINCENT J; REICH SIEGFRIED HEINZ; RODRIGUEZ MICHAEL J; SHEPHERD TIMOTHY A; TATLOCK JOHN H; JUNGHEIM LOUIS NICKOLAUS
权利人:AGOURON PHARMA
摘要:HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optionally other anti-viral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.

专利号:US-2003083383-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