Numbering Code	U-PHA00 3C902 PJ86	Year/Term	2022 ・ First semester
Number of Credits	4	Course Type	Practical training
Target Year	3rd year students or above	Target Student
Language	Japanese	Day/Period
Instructor name	HATTORI AKIRA (Graduate School of Pharmaceutical Sciences Associate Professor) Naka Hiroshi (Graduate School of Pharmaceutical Sciences Associate Professor) INUKI SHINSUKE (Graduate School of Pharmaceutical Sciences Associate Professor) TAKIKAWA HIROSHI (Graduate School of Pharmaceutical Sciences Senior Lecturer) YAMAOKA YOUSUKE (Graduate School of Pharmaceutical Sciences Assistant Professor) KURANAGA TAKEFUMI (Graduate School of Pharmaceutical Sciences Assistant Professor) NANJO TAKESHI (Graduate School of Pharmaceutical Sciences Assistant Professor) Arichi Norihito (Graduate School of Pharmaceutical Sciences Assistant Professor) KURODA YUSUKE (Graduate School of Pharmaceutical Sciences Program-Specific Assistant Professor)
Outline and Purpose of the Course	Learn the basic operations required for organic chemistry experiments through practical training in the synthesis and purification of organic compounds. Practice basic, functional group conversion and complement that knowledge by observing actual reactions. Learn through practical means the multi-step synthesis of natural alkaloids, bronchodilators, antiepileptic drugs, and peptides. In addition, students will practice handling microbial metabolites, crude drugs, and medicinal plants used as pharmaceuticals, learning how to isolate and identify natural organic compounds. They will also learn labeling methods, target-protein-identification methods, crude-drug-discrimination methods, and ways of preparing crude-drug preparations.
Course Goals	1. Pay attention to the handling of dangerous substances and harmful chemicals, and carry out experiments safely. 2. Take appropriate experimental records and compile and report them. 3. Handle typical organic-chemistry laboratory equipment appropriately. 4. Learn the basic operations of glassworking and create simple glassware. 5. Accurately and precisely weigh liquids and solids and quickly calculate the amount of a substance. 6. Identify the appropriate purifying method, based on the organic compound. 7. Identify compounds by measuring and analyzing basic spectral data. 8. Detect the characteristic structure and functional groups of compounds through color reactions. 9. Introduce and convert basic functional groups. 10. Construct a typical carbon skeleton to synthesize compounds, including pharmaceuticals. 11. Select an appropriate protecting group, introduce, and then remove it. 12. Perform peptide synthesis correctly by suppressing racemization. 13. Perform basic operations to label natural organic compounds and identify target proteins. 14. Properly handle crude drugs and medicinal plants and distinguish unknown specimens.
Schedule and Contents	Some of the following items will be included in the actual training. Students will be contacted in advance with details of the training content. [A] Introductory lecture/practice 1. Introductory lecture 2. Glassworking 3. Recrystallization 4. Extraction 5. Distillation 6. TLC and column chromatography [B] Synthesis of organic compounds I Functional group conversion of aromatic compounds and the synthesis of natural alkaloids 1. Total synthesis of natural alkaloid xylopinin (1) 2. Total synthesis of natural alkaloid xylopinin (2) 3. Total synthesis of natural alkaloid xylopinin (3) 4. Total synthesis of natural alkaloid xylopinin (4) 5. Ester distillation and Grignard reaction 6. Discussion and consideration of total alkaloid synthesis and Grignard reactions [C] Synthesis of organic compounds II Synthesis of theophylline and phenytoin 1. Dehydration-condensation reaction of dimethylurea and cyanoacetic acid 2. Nitrosation reaction 3. Reduction and formylation reactions 4. Theophylline synthesis and benzoin-condensation reaction 5. Oxidation reaction 6. Synthesis of phenytoin [D] Synthesis of organic compounds III Peptide chemistry and aspartame synthesis 1. Diels-Alder reaction 2. Synthesis of racemization inhibitor HONB 3. Synthesis of phenylalanine methyl ester 4. Protection of amino groups by Z conversion 5. Synthesis of protected dipeptides by condensation 6. Aspartame synthesis [E] Natural organic compounds Handling of natural organic compounds and the identification of target proteins 1. Probe spacer protection 2. Condensation of spacer and biotin 3. Synthesis of biotinylated cyclosporin A 4. Isolation and purification of cyclosporin A target protein 5. Detection of cyclosporine A target protein [F] Crude drugs and medicinal plants Handling of crude drugs and medicinal plants 1. Medicinal-botanical garden training and shiunkou formulation 2. Appraisal of powdered crude drugs (1) 3. Appraisal of powdered crude drugs (2)
Evaluation Methods and Policy	As a general rule, students are expected to participate in all of the training. Evaluation is based on the following: normal score 50%; and reports 50%. The normal score includes attendance, skills and attitudes, understanding of experimental operations, awareness of safety, consideration of experiments, and discussions during practical training. The report will be scored, based on lab notebooks, preparatory study, assignment reports, and other work.
Course Requirements	None
Study outside of Class (preparation and review)	Before each training session, prepare by studying the background and purpose of the experiment and gathering information about the instruments and reagents used, the procedure of the experiment, and the expected results.
Textbooks	Textbooks/References	“Practice book”
References, etc.	Introduced during class
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