lec_1 - CHEMISTRY 124/224 ORGANIC STRUCTURE ANALYSIS Dr....

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CHEMISTRY 124/224 ORGANIC STRUCTURE ANALYSIS Dr. Taro Amagata Project Scientist, UC Santa Cruz EMAIL amagata@chemistry.ucsc.edu
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LECTURE ONE 1. Verifying or Creating Structural Drawings 2. The Expressway (i.e. Concise Approaches) to Structure Determination 3. Types of Structure Elucidation Problems 4. Brief History 5. The Four Techniques & Their Relative Merits 6. The Steps – An Overview 7. Important Resources 8. A Problem to be Solved
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TWO DIMENSIONAL THREE DIMENSIONAL Organic Molecular Structures What are “ORGANIC COMPOUNDS”? Chemical compounds with carbon atom backbone C-C and C-H bond Diamond? CO 2 , CO? H 2 CO 3 ?
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STRUCT DRAWINGS SHOW 2D FRAME WORK 1 CARBON SKELETON 1 FUNCTIONAL GPS 1 LOCATION OF FGs 3D FRAME WORK 1 RELATIVE STEREO 2 ABSOLUTE STEREO 3 CONFORMATIONAL FEATURES
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VERIFYING OR CREATING STRUCTURAL DRAWINGS 1. A COMMON TASK 2. MANY ELEMENTS 3. DEFINING STEREO STRUCTURES 4. THE STRATEGIES
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VERIFYING OR CREATING STRUCTURAL DRAWINGS 1. A COMMON TASK: A FASCINATING LIST: C 46 N 7-11 O 7-11 . NH NH N H N N HN N O O NH O NH NH 2 HN O O O O NH HO CH 3 N NH NH HN HN O O O N H O O N H O O OH hymenamide A mozamide B N H H N N H O O N NH H N O N NH N H O O O O O O Br OH N HN NCH 3 N H O NH O O O O N H H N OH O OCH 3 O O dehydrodolastatin 13 orbiculamide A HN H N N H O O O H N O O O O H N O N H HO OH HN O NCH 3 O N H O HN HN N H OH O N H O O N H O O HO OH H N NH 2 NH kahalalide A anabaenopeptin H HN OH O O N O NH O O HN N O NH NH O H 2 N O OH kahalalide K nostophycin O O O H N O HN NH NH O HN N O OH O H 2 N O O OH
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Engineered Biosynthesis of Type I PKS - DEBS from S. erythraea S H 3 C O S O H 3 C S O H 3 C HO CH 3 HO CH 3 HO CH 3 O H 3 C HO CH 3 HO CH 3 S O CH 3 O H 3 C HO CH 3 HO CH 3 CH 3 S O CH 3 O H 3 C HO CH 3 HO CH 3 CH 3 CH 3 S O CH 3 HO O H 3 C HO CH 3 HO CH 3 CH 3 CH 3 CH 3 HO S O HO CH 3 O O O HO H 3 C OH CH 3 H 3 C CH 3 CH 3 Module 5 Module 6 Module 2 CH 3 Module 1 Module 3 CH 3 AT ACP KS AT KR ACP KS AT KR ACP KS AT ACP KS AT DH ER KR ACP KS AT KR ACP KS AT KR ACP TE OH Module 4 6-deoxyerythronolide B Erythromycin A O O O HO H 3 C OH CH 3 CH 3 CH 3 CH 3 CH 3 OH 10-desmethyl -6-deoxyerythronolide B 10-Desmethyl erythromycin A mmAT mAT 2. CREATING STRUCTURAL DRAWINGS: MANY ELEMENTS
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CHIRALITY: RELATIONSHIPS AMONG ISOMERS 3. DEFINING STEREO STRUCTURES
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COURSE FOCUS FOUR TECHNIQUES NMR MS IR UV-VIS DESIRED OUTCOMES MF ID OF FCN GROUPS CH, CC, CZ, OR RINGS FCN GP POSITIONS REGIOCHEM STEREOCHEM 1) OBTAIN DATA 1) INTERPRET SPECTRA 4. CONCISE APPROACHES
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lec_1 - CHEMISTRY 124/224 ORGANIC STRUCTURE ANALYSIS Dr....

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