药物 作用 有效成分另一对映体作用 反应停 镇静 S R致畸 Thalidomide 乙胺丁醇 抗结核 SS RR导致失明 心得安 心脏病 S R抑制性欲 Propranolol 氯霉素 抗菌 S R抗菌活性低 萘必洛尔 治疗高血压 右旋 左旋舒张血管 酮基布洛芬 抗炎 S R防治牙周病 ketoprofen
药 物 作用 有效成分 另一对映体作用 反应停 镇静 S R 致畸 Thalidomide 乙胺丁醇 抗结核 SS RR 导致失明 心得安 心脏病 S R 抑制性欲 Propranolol 氯霉素 抗菌 S R 抗菌活性低 萘必洛尔 治疗高血压 右旋 左旋 舒张血管 酮基布洛芬 抗炎 S R 防治牙周病 ketoprofen
Worldwide sales of chiral drugs 2017 5.1 billion 1500 1330 1180 盼 1200 uo! 900 06 614 600 350 300 19931994199519961997199819992000 Chem.Eng.News,2001,Vol.79,No.40,pp79 6,000 5,000 4,000 3,000 2,000 1,000 200g 2010 2011 2016 ☐Chiral synthesis 回Chiral analysis ☐Chiral resolution Source:BCC Research
Chem. & Eng. News, 2001, Vol. 79, No. 40, pp79 350 452 614 812 1330 706 934 1180 0 300 600 900 1200 1500 1993 1994 1995 1996 1997 1998 1999 2000 100 million $ Worldwide sales of chiral drugs 2017 5.1 billion
Sec1 Chirality手性 "Handedness":right glove doesn't fit the left hand. -Mirror-image object is different from the original object. right hand left hand Copyright 2005 Pearson Prentice Hall,Inc
Sec 1 Chirality 手性 ▪“Handedness”: right glove doesn’t fit the left hand. ▪Mirror-image object is different from the original object
Chirality A molecule is chiral if its two mirror image forms are not superposable upon one another. A molecule is achiral if its two mirror image forms are superposable. ◆ ◆ ◆ left hand right hand left hand ◆ right hand plus mitten plus mittne plus left glove■ plus right glove ◆ ◆ ● ● : ◆ ◆ left hand right hand plus right glove plus left glove left hand right hand plus mug plus mug
Chirality ❖A molecule is chiral if its two mirror image forms are not superposable upon one another. ❖A molecule is achiral if its two mirror image forms are superposable
Bromochlorofluoromethane is chiral It cannot be superposed point for point on its mirror image. CI Br 111111111111 B H To show nonsuperposability,rotate this model 180 around a vertical axis
Br Cl H F Bromochlorofluoromethane is chiral H Cl Br F To show nonsuperposability, rotate this model 180° around a vertical axis. ❖It cannot be superposed point for point on its mirror image