(This question paper consists of 6 questions on 7 printed pages) (Kertas ini mengandungi 6 soalan dalam 7 halaman yang dicetak)
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1 UNIVERSITY OF MALAYA UNIVERSITI MALAYA EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE PEPERIKSAAN IJAZAH SARJANA MUDA SAINS ACADEMIC SESSION 2012/2013 : SEMESTER 1 SESI AKADEMIK 2012/2013 : SEMESTER 1 SCES3321 : Kimia Biosynthesis Biosintesis Chemistry January 2013 Januari 2013 Time : 2 hours Masa : 2 jam INSTRUCTIONS TO CANDIDATES: ARAHAN KEPADA CALON: Answer ALL questions. Jawab SEMUA soalan.. (This question paper consists of 6 questions on 7 printed pages) (Kertas ini mengandungi 6 soalan dalam 7 halaman yang dicetak)
2 SCES3321/02 Answer ALL questions. 1. (a) Provide names ( or general names) for the molecules or building blocks (I) to (V) and identify biosynthetic pathways for the synthesis of compounds (III), (IV) and (VI). (Systematic nomenclature and detailed mechanisms are not required). Berikan nama (atau nama am) bagi molekul atau building blocks (I) hingga (V) dan kenal pasti jalan sintesis biologi untuk sintesis sebatiansebatian (III), (IV) dan (VI). (Penamaan sistematik dan mekanisma lengkap tidak diperlukan) ( 9 marks/markah) Provide a mechanism for the biosynthesis of (III) from (V). Berikan suatu mekanisme untuk biosintesis bagi (III) dari (V). (6 marks/markah)
3 SCES3321/03 2. By means of retrosynthetic analysis, derive the polyketide building blocks necessary for the biosynthesis of (I) and (II). Menggunakan analisis sintesis retro, berikan kerangka struktur polyketide yang diperlukan untuk biosintesis bagi (I) dan (II). (8 marks/markah) 3. A concise biosynthetic pathway leading to usnic acid (IV) and its regioisomer (V) is provided below: Kaedah biosintesis lengkap untuk asid usnik (IV) dan regioisomer (V) diberikan di bawah:
4 SCES3321/04 3. (a) Provide a mechanism for the synthesis of the tetraketide (I) above. Berikan satu mekanisme bagi sintesis tetrakitida (I) di atas. Draw all resonance forms for the phenoxy radical (III). Lukiskan semua bentuk resonans bagi radikal fenoksi (III) (3 marks/markah) (c) Draw out a mechanism for the conversion of (III) to (V). Lukiskan mekanisme untuk penukaran (III) kepada (V) (6 marks/markah) 4. Draw out a biosynthetic mechanism for the transformation of farnesyl pyrophosphate ( 1 ) to any three of the target molecules (2) to (6). Lukiskan mekanisme biosintesis bagi penukaran farnasil pirofosfat (1) kepada mana-mana tiga molekul sasaran (2) kepada (6). (14 marks/markah)
5 SCES3321/05 5. The following scheme shows selected chemical reactions of the biosynthesis of terpenes. Skema tindak balas berikut mununjukkan tindak balas kimia terpilih untuk biosintesis terpena. (a) Name the primary enzyme class for the reactions A, C, D and E. Namakan kelas enzim primer bagi tindak balas A, C, D dan E. Explain the chemical selectivity of the aldol-type reaction A with respect to the carbonyl groups. Jelaskan keterpilihan kimia bagi kumpulan karbonil untuk tindak balas jenis aldol A. (2 marks/markah) (c) Provide a detailed mechanism for reaction B. Berikan mekanisma terperinci untuk tindak balas B. (d) What is the function of the diphosphate ester group in compound F? Provide a chemical equivalent to substitute the ester group in a synthetic laboratory. Apakah fungsi ester difosfat dalam sebatian F. Berikan kumpulan kimia berfungsi yang biasa untuk menggantikan ester ini dalam makmal kimia. (2 marks/markah)
6 SCES3321/06 (e) (i) Draw the structural formula for the nicotine amide based cores in NADP + and NADPH. Lukis formula struktur bagi struktur teras nikotinamida dalam NADP + dan NADPH. (ii) What is the driving force for the reaction of NADPH to NADP +? Apakah daya penggerak bagi tindak balas NADPH kepada NADP +? (iii) Indicate a synthetic chemical equivalent for NADPH. Apakah reagen kimia sintetik tipikal untuk menggantikan NADPH. (5 marks/markah) (f) A labeling experiment aiming on reaction A involves the following two compounds: Eksperimen pelabelan untuk tindak balas A melibatkan dua sebatian berikut: (i) (ii) Provide the structural formula of compound F indicating the position of all isotopes, assuming 100 % isotopic labeling and no biochemical background. Berikan formula struktur sebatian F yang menunjukkan 100 % pelabelan isotop untuk semua sebatian dan tiada gangguan biokimia Construct the 13 C-NMR spectrum of compound F based on the istopic distribution in (i). Lakar spektrum NMR 13 C bagi sebatian F menunjukkan kriteria dalam (i). [ppm] CH 3 : 26 (E), 17(Z); C: 135; CH: 124; CH 2 : 60 (iii) (iii) Sketch the 13 C-NMR spectrum of F assuming that precursors are only 50% isotopically labeled. Lakar spektrum NMR 13 C bagi sebatian F yang menunjukkan 50 % pelabelan isotop untuk semua prekursor. Where does the biochemical background in a labeling experiment come from? Dari manakah gangguan biokimia datang dalam eksperimen pelabelan. (8 marks/markah)
7 SCES3321/07 6. Multiple unsaturated fatty acids are essential precursors for hormones. Their biosynthesis originates from linolenic acid (18:2-6). Asid lemak politaktepu adalah prekursor penting untuk hormon. Biosintesis mereka berasal daripada asid linolenik (18:2-6). (a) Draw the structural formula for linolenic acid. Lukis formula struktur untuk asid linolenik. Write the entire reaction sequence (all reactions but without mechanistic details) for the conversion of free linolenic acid (18:2-6) to EPA (20:5-3). Berikan tertib tindak balas (semua tindak balas tapi bukan mekanisma) untuk sintesis biokimia EPA (20:5-3) daripada asid lenolenik (18:2-6). (10 marks/markah) (c) Design a labeling experiment to prove that arachidonic acid (20:4-6) originates from linolenic acid (18:2-6) based on the assumption that arachidonic acid can be easily isolated from cell extracts. Reka eksperimen pelabelan untuk membuktikan asid arakidonik (20:4-6) barasal dari asid linolenik (18:2 w-6) berdasarkan anggapan bahawa asid arakidonik diasingkan dengan mudah daripada ekstrak sel. (i) (ii) Identify a suitable isotope and indicate the detection technique. Explain your answer. Kenal pastikan isotop yang sesuai dan nyatakan teknik pengesanan. Jelaskan pilian anda. Does the labeling require a specific position? Explain. Adakah pelabelan memerlukan kedudukan tertentu? Jelaskan. (6 marks/markah) (d) Provide a mechanistic explanation for the following biochemical conversion. Berikan mekanisma untuk tindak balas biokimia berikut. (5 marks/markah) *******************
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