(Kertas ini mengandungi 5 soalan dalam 7 halaman yang dicetak) (This question paper consists of 5 questions on 7 printed pages)

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1 UNIVERSITI MALAYA UNIVERSITY F MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATIN FR THE DEGREE F BACHELR F SCIENCE SESI AKADEMIK 2014/2015 : SEMESTER 1 ACADEMIC SESSIN 2014/2015 : SEMESTER 1 SCES3321 : KIMIA BISINTESIS BISYNTHESIS CHEMISTRY Disember 2014/Januari 2015 December 2014/January 2015 Masa : 2 jam Time : 2 hours ARAHAN KEPADA CALN : INSTRUCTINS T CANDIDATES : Jawab SEMUA soalan. Answered ALL questions. (Kertas ini mengandungi 5 soalan dalam 7 halaman yang dicetak) (This question paper consists of 5 questions on 7 printed pages)

2 1. Skim berikut menunjukkan sintesis biokimia asid arakidonik. The following scheme shows the biosynthesis of arachidonic acid. (a) Tentukan angka x, y dan z dalam sebatian A. Specify the numbers for x, y and z in compound A. (2 markah/marks) (b) Namakan kelas enzim primer bagi tindak balas B, G dan K. Name the primary enzyme class for the reactions B, G and K. (3 markah/marks) (c) Berikan mekanisma untuk tindak balas D dan jelaskan peranan tindak balas C. Provide a mechanism for reaction D and explain the function of reactions C. 2/7

3 (d) Apakah fungsi tindak balas B dalam urutan biokimia di atas. Berikan tindak balas kimia yang biasa dalam makmal kimia. What is the function of reaction B in the biochemical sequence above? Provide a chemical equivalent to be used in a synthetic lab. (2 markah/marks) (e) Berikan mekanisma terperinci untuk tindak balas E. Provide a detailed mechanism for reaction E. (f) Lukis struktur teras untuk NADPH dan jelaskan mengapa NADPH/NADP + boleh digunaan sebagai sistem redoks biokimia berbalik. Berikan reagen kima yang biasa dalam makmal kimia untuk NADPH. Draw the core structure of NADPH and explain why NADPH/NADP + can be used as a reversible biochemical redox-system. Provide a chemical equivalent for NADPH. (5 markah/marks) (g) Berikan mekanisma untuk tindak balas H. Provide a mechanism for reaction H. (h) Berikan mekanisma disederhanakan untuk tindak balas I. Provide a simplified mechanism for reaction I. (i) Lukis struktur sebatian L dan jelaskan pentingnya biokimia. Provide a structure of compound L and explain its biological importance. (5 markah/marks) (j) Reka eksperimen pelabelan untuk hubungan biokimia 18:2( -6), A, dan 20:4( -3), I: Nyatakan bahan yang dilabel bermula, serta jenis pelabelan dan kaedah pengesanan. Jelaskan pilihan anda. Design a labeling experiment to prove the biochemical relationship between 18:2( -6), A, and 20:4( -3), L: Specify the labeled starting material, as well as labeling type and detection method. Explain your choice. (5 markah/marks) 3/7

4 2. Biosintesis alanin adalah berdasarkan tindak balas berikut. The biosynthesis of alanine is based on the following conversion. H 2 N H (CH 2 ) 3 C 2 H + CH 3 H H (CH 2 ) 3 C 2 H + H 2 N CH 3 H M N P (a) Reka eksperimen pelabelan untuk hubungan biokimia P dengan M dan N; menunjukkan jenis dan kedudukan isotop di bahan awal dan hasil dijangka. Design an NMR-based labeling experiment to prove the biochemical relation of P with M and N; indicate the type and position of isotops in the starting materials and the expected product. ( 13 C for P: 180 ppm, 20 ppm, CH 50 ppm) (b) Berikan spektrum 13 C-NMR untuk hasil mengenali dalam a, mengunakan 100% labeling isotop dan kandungan semula jadi 13 C ~10%. Predict the 13 C-NMR spectrum for the product identified in a, assuming 100% isotopic labeling and a natural 13 C-content of ~10%. (c) Berikan spektrum 13 C-NMR untuk P dalam 13 CDH 2 13 CH(NH 2 ) 12 C 2 H. Predict the 13 C-NMR spectrum for P according to 13 CDH 2 13 CH(NH 2 ) 12 C 2 H. 4/7

5 3. (a) Kenalpastikan blok binaan utama bagi metabolisme sekunder yang menghasilkan molekul di bawah: Identify the principal building blocks of secondary metabolism leading to the molecules shown below: (6 markah/marks) (b) Tunjukkan mekanisme biosintesis terperinci bagi salah satu molekul berikut: Provide a detailed mechanism for the biosynthesis of any one of the three molecules shown below: (12 markah/marks) 5/7

6 4. ksidatif fenolic berganding acetophenone triol (1) menghasilkan produk (ii), (iii) dan (iv). Sediakan mekanisme terperinci untuk biosintesis (i), (ii) (iii) and (iv). The acetophenone triol (1) is transformed to the products (ii), (iii) and (iv) by oxidative phenolic coupling. Provide detailed mechanisms for the biosynthesis of (i), (ii) (iii) and (iv) (18 markah/marks) 6/7

7 5. Lukiskan mekanisme tindak balas untuk menghasilkan tiga daripada lima produk berikut: Draw out reaction mechanisms for the construction of any three of the following five products (14 markah/marks) TAMAT END 7/7

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