第十六部分氨基酸教学 ppt课件

1、R-CH-COONH2碱性溶液中R-CH-COONH3H+OH-两性离子H+OH-R-CH-COOHNH3酸性溶液中R-CH-COOHNH2H2NHCOOHR H2NCH2COOHCH3-CH-COOHNH2(CH3)2CH-CH-COOHNH2(CH3)2CHCH2-CH-COOHNH2C2H5CH-CH-COOHNH2CH3C6H5CH2-CH-COOHNH2HSCH2-CH-COOHNH2CH3CH-CH-COOHNH2OHH2NCO(CH2)2CH-COOHNH2H2NCOCH2CH-COOHNH2CH3S(CH2)2CH-COOHNH2HOCH2CH-COOHNH2NCOOHH CH

2、2CH-COOHNH2HONHCH2CH-COOHNH2CH2CH-COOHNH2HOOCHOOC(CH2)2CH-COOHNH2 H2N(CH2)4CH-COOHNH2H2NCNH(CH2)3CH-COOHNH2NHCH2CH-COOHNH2NNHNO2NO2FH2NCHCO(HNCHCO)nRR+亲核取代NO2NO2NHCHCOOHR黄色物质OOOH2OOONCHCOOHR-CO2H2NCHCOOHROOOHOH水合茚三酮亲核加成OONCH2ROHON=OO紫色物质OON=OO氨的衍生物与醛亲核加成的产物水解异构化H2OOONH2RCHO+OON=CHROOOHOH 氨基酸的合本钱质上就是

3、在羧酸的-位引入一个氨基的过程，可归结为亲核取代和亲核加成两种根本方法。 RCH2COOHBr2PRCHCOOHBrNH3高温高压RCHCOOHNH2(dl)CH3CH2COOHBr2PCH3CHCOOHBrNH3高温高压CH3CHCOOHNH2(dl)RCHOHCNR-CH-CNOHNH3R-CH-CNNH2H3+OR-CH-COOHNH2(dl)HCNNH3CH2CHOH3+OCH2CHCNNH2NaOHH2O(dl)CH2CHCOOHNH2NHOOK2CO3NKOORCHCOOC2H5XSN2亲核取代NOOCHCOOC2H5ROH-H2OOOOORCHCOONH2+H3+ORCHCOOH

4、NH2(dl)NOOCH(COOC2H5)2NKOOBrCH(COOC2H5)2CH2(COOC2H5)2Br2CCl4NaOCH3NOC(COOC2H5)2ORX亲核取代NOC(COOC2H5)2OR1. OH-/H2O2. H3+ORCHCOOHNH2(dl)RCH=CHCOOC2H5Michael加成NOCHCH2COOC2H5ORC(COOC2H5)21. OH-/H2O2. H3+OHOOCCH2CHCHCOOHNH2(dl)RONOCH(COOC2H5)2CH3S(CH2)2ClNaOCH3NOC(COOC2H5)2OCH2CH2SCH31. OH-/H2O2. H3+OCH3S(

5、CH2)2CHCOOHNH2(dl)蛋氨酸(50%)CH2=CHCOOC2H5NaOCH3NOCH2CH2COOC2H5OC(COOC2H5)21. OH-/H2O2. H3+OHOOCCH2CH2CHCOOHNH2(dl)谷氨酸(75%)CH2(COOC2H5)2HNO2该氢原子可以在强碱性介质中脱出，形成负碳离子 O=N-CH(COOC2H5)2 HO-N=C(COOC2H5)2H2/Pt(CH3CO)2OCH3CONHCH(COOC2H5)2NHCOOH(dl)脯氨酸分子内亲核取代反应CH3CONHC(COOC2H5)2(CH2)3BrOH-H2OCH3CONHCH(COOC2H5)2B

6、r(CH2)3BrNaOC2H5COOCOOH2NBrNHCOOCOOH3+OCH3CONHCH(COOC2H5)2NaOC2H5NNHCH2ClNNHCH2C(COOC2H5)2NHCOCH3OH-H2OH3+ONNHCH2CHCOOHNH2(dl)组氨酸NHCH2N(CH3)2NCH2草绿碱CH3CONHCH(COOC2H5)2NaOC2H5OH-H2OH3+ONHCH2CNHCOCH3COOC2H5COOC2H5(dl)色氨酸NHCH2CHCOOHNH2CH3CONHCH(COOC2H5)2NaOC2H5HCHOHOCH2C(COOC2H5)2NHCOCH3CH3CONHCH(COOC2H5)2NaOC2H5CH3CHOCH3CHC(COOC2H5)2NHCOCH3HOOH-H2OH3+OCH3CHCHCOOHNH2(dl)OHOH-H2OH3+OHOCH2CHCOOHNH2(dl) 氨基酸的合成实践上就是运用负碳离子反响的实例，特别是乙酰氨基丙二酸二乙酯法已成为普遍运用的方法。以上方法得到的氨基酸均为外消旋体，假设需求得到某一