西北农林科技大学：《有机化学 Organic chemistry》课程PPT教学课件（2013）Chapter 06 Stereochemistry

Organic Chemistry,6th Edition L.G.Wade,Jr Chapter 6 Stereochemistry

Chapter 6 Stereochemistry Organic Chemistry, 6th Edition L. G. Wade, Jr

Organic Chemistry,6th Edition L.G.Wade,Jr. Chapter 6 Stereochemistry Key Notes Chiralenantiomers;Chirality Chiral center;Optical rotations;R/S,D/L;Diastereomers;mesoforms; Resolution of enantiomers;

Chapter 6 Stereochemistry Organic Chemistry, 6th Edition L. G. Wade, Jr. Key Notes Chiral enantiomers; Chirality & Chiral center; Optical rotations; R /S ，D/L; Diastereomers ; meso forms; Resolution of enantiomers;

Contents Molecular Chirality Chiral carbon Absolute and Relative Configuration Stereoisomers without chiral carbons Properties of Enantiomers Diastereomers Resolution of Enantiomers

Contents ❖Molecular Chirality & Chiral carbon ❖Absolute and Relative Configuration ❖Stereoisomers without chiral carbons ❖Properties of Enantiomers & Diastereomers ❖Resolution of Enantiomers

Biological Significance of Chirality Since most of the natural (biological)environment consists of enantiomeric molecules (amino acids, nucleosides,carbohydrates and phospholipids are chiral molecules),then enantiomers will display different properties.Then,in our body: Enantiomers Drug Enzyme Tight Binding Weak Binding

◆Biological Significance of Chirality

Biological Significance 必 比旋光度 mp 肌肉运动--乳酸是右旋体，（+)-乳酸+3.82° 53°C 糖发酵乳酸是左旋体，(·)-乳酸 -3.82° 53C 牛奶变酸外消旋体，（士）·乳酸 无旋光性 18°C Enantiomers of Epinephrine H3C⊕ Enzyme Anionic Flat area Anionic Flat area site site Not Occupied Occupied (+)-Epinephrine (-)-Epinephrine Poorer Fit Less Active Better Fit More Active

Biological Significance ❖ 比旋光度 mp ❖肌肉运动---乳酸是右旋体，（+）-乳酸 + 3.82° 53℃ ❖糖发酵---乳酸 是左旋体，（﹣）- 乳酸 - 3.82° 53℃ ❖牛奶变酸---外消旋体， （±）- 乳酸 无旋光性 18℃

Biological Discrimination OH OH 生物鉴别 CH2一NH HO CHy (R)-(-)-epinephrine enzyme active site enzyme-substrate complex natural epinephrine 肾上腺素 used in medicine as a heart stimulant, OH OH vasoconstrictor,and bronchial relaxant. 白色到褐色之间的晶体 NH2一CH OH 化合物.用作心脏兴奋剂、 H 血管收缩剂和支气管肌 松弛剂 (S)-(+)-epinephrine unnatural epinephrine does not fit the enzyme's active site

Biological Discrimination 肾上腺素 used in medicine as a heart stimulant, vasoconstrictor, and bronchial relaxant. 白色到褐色之间的晶体 化合物.用作心脏兴奋剂、 血管收缩剂和支气管肌 松弛剂 生物鉴别

Me2N. Ph 0 darvon enzyme Darvon is a painkiller. Its enantiomer is an anticough agent. 手性药物chiral drugs Why to resolve the racemic mixtures to obtain the single enantiomer?

手性药物chiral drugs Why to resolve the racemic mixtures to obtain the single enantiomer?

Many pharmaceuticals are chiral! COOH Ibuprofen (Advil) Thalidomide: used as a sedative and anti-nausea drug

N N O O O O H H COOH H Many pharmaceuticals are chiral! Ibuprofen (Advil) Thalidomide: used as a sedative and anti-nausea drug * *

Other times,the different interaction of enantiomers with chiral biological molecules is serious. The two enantiomers of Thalidomide: beneficial sedative and anti-nausea drug Caused serious birth defects when taken by pregnant women!

N N O O O O H H N N O O O O H H Other times, the different interaction of enantiomers with chiral biological molecules is serious. * The two enantiomers of Thalidomide: beneficial sedative and anti-nausea drug * Caused serious birth defects when taken by pregnant women!

手性药物 Why to resolve the racemic mixtures to obtain the single enantiomer? 镇静 thalidomide 反应停

※Why to resolve the racemic mixtures to obtain the single enantiomer? thalidomide N N O O O O * 手性药物 反应停 镇静