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翻譯:扈棽棽(簡介並寄信)
編輯:李曉廬(簡介並寄信)

2003年春季

5.32 是一門15個學分的課程,該實驗工作較5.310和5.311複雜,課程的重點內容是手性催化條件下的有機合成,物質的純化,以及利用諸如紅外光譜,1D和2D核磁共振譜,紫外分光光度法,質譜分析,薄層色層分析,非手性和手性氣相色層分析法對有機化合物進行分析。在5.32這門課程中,實驗內容也牽涉到酵素的提純,表徵,測定以及有機和生物化學合成過程中的分子建模問題。

講師:

Alexander M. Klibanov 教授

實驗室主任:

Mircea D. Gheorghiu 博士


1. Diels-Alder 反應的不對稱催化作用 (PDF). Diels-Alder 反應附錄 (PDF)

該實驗牽涉到利用不對稱路易士酸催化α,β-不飽和羰基化合物使其生成環狀或非環狀的二烯烴的Diels-Alder環加成反應。手性硼催化劑是從L-或D-酒石酸開始合成的。對映異構體過量值由手性氣相色層分析和/或旋光測定法測得。用半經驗和ab-initio計算可以算出 外向- 和 內向-型的非對映異構體的熱力學相對穩定性,以及由硼催化劑和 α,β-不飽和羰基化合物所組成的複合物的結構。

2. 定性有機分析 (PDF)

首先會向你提供一個由芳香族的酸和一個中性化合物組成的混合物。經過分離和純化後,要對兩種成分進行鑑定:測定芳香族的酸及其胺基化合物的熔點和 1H核磁共振的數據;測定中性化合物的熔點,紅外光譜,紫外光譜,核磁共振 (1H, 13C, DEPT, gCOSY, HETCOR (HMQC) 和GC-MS的數據。

3. 生物化學 (PDF)

可以利用氣相色層分析,對細菌酵素的粗產物進行純化。需要對經過純化的細菌酵素進行表徵和測定其動力學參數。通過比較從自然品種和變異品種測定的數據,並且通過電腦建模的手法,可以闡明所觀察到的酵素受質的結構跟酵素分子的結構之間存在的差異。

4. 文獻研究報告

學生要從給定的50種化合物中任選一種,利用Beilstein Commander2002 和 Scifinder2002電腦程式和麻省理工學院圖書館提供的文獻資料對該化合物進行文獻研究。研究完成後,每位元學生需要進行15分鐘的口頭報告,描述該化合物的結構,發現,物理和化學性質,以及關於該化合物書面報告的應用。利用在口頭陳述中講師和同學反饋的意見,每位學生要寫出15-20頁的書面報告(剛好滿足麻省理工學院要求的寫作要求)。


Spring 2003

5.32 is a 15 unit class. Experimental work more advanced than in 5.310 or 5.311, emphasizing organic synthesis assisted by chiral catalysis, purification, and analysis of organic compounds employing such methods as IR, 1D and 2D NMR, UV spectroscopies and mass spectrometry, and thin layer and non-chiral and chiral gas chromatography. Also experiments involving enzyme purification, characterization and assays, as well as molecular modeling in organic synthesis and in biochemical systems.

Instructor

Prof. Alexander M. Klibanov

Laboratory Director

Dr. Mircea D. Gheorghiu


1. Asymmetric Catalysis of Diels-Alder Reactions (PDF). Diels Alder Appendix (PDF)

This experiment involves the asymmetric Lewis acid catalyzed Diels-Alder cycloaddition of an α,β-unsaturated carbonyl compounds to a cyclic or acyclic diene. A chiral boron catalyst is synthesized starting from L- or D-tartaric acid. The ee is assessed by chiral GC and/or polarimetry. The relative thermodynamic stabilities of the exo- and endo-diastereomers, and the structure of the complexes of the boron catalysts with the α,β-unsaturated carbonyl compound are computed at semiempirical and ab-initio levels.

2. Qualitative Organic Analysis (PDF)

A mixture of an aromatic acid and a neutral compound is provided. After their separation and purification, the two components are identified: the aromatic acid from its melting point (mp) and that of its amide and 1H NMR data; the neutral compound from its mp, IR, UV, NMR (1H, 13C, DEPT, gCOSY, HETCOR (HMQC), and GC-MS.

3. Biochemistry (PDF)

A crude preparation of a bacterial enzyme will be subjected to purification using various chromatographies. The resultant purified enzyme will be characterized, and its kinetic parameters will be determined. By comparing those for the wild-type and mutant enzymes, and by performing computer modeling of their structures with the substrate, the molecular rationale for the observed differences will be elucidated.

4. Literature Report

A student will select a chemical compound out of some 50 posted. Then (s)he will carry out a literature search concerning this compound assisted electronically by the Beilstein Commander 2002 and SciFinder2002 computer programs and literature sources available at the MIT libraries. After that, each student will present a 15-min oral report describing the structure, discovery, physical and chemical properties, and applications of the selected compound. Using the feedback obtained from the instructors and the fellow students during the oral presentation, the student will then prepare a 15-20 page written report (which also can be submitted to satisfy the MIT writing requirement).


 
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