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1 UNIVERSITI MALAYA UNIVERSITY OF MALAYA PEPERIKSAAN IJAZA SARJANA MUDA SAINS EXAMINATION FOR TE DEGREE OF BACELOR OF SCIENCE SESI AKADEMIK 2016/2017 : SEMESTER 1 ACADEMIC SESSION 2016/2017 : SEMESTER 1 SID2004 : KIMIA BIOORGANIK BIOORGANIC CEMISTRY Dis 2016/ Jan 2017 Dec 2016/ Jan 2017 MASA : 2 jam TIME : 2 hours ARAAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Jawab SEMUA soalan. Answer ALL questions. (Kertas soalan ini mengandungi 4 soalan dalam 10 halaman yang dicetak) (This question paper consists of 4 questions on 10 printed pages)
2 1. (a) Adakah anda setuju bahawa semua gula yang menunjukkan fenomena mutarotation adalah gula penurun? Mengapa? Anda boleh gunakan glukosa untuk menerangkan jawapan anda. Do you agree that all sugars which undergo mutarotation are reducing sugars? Why? You may use glucose to illustrate your answer. (3 markah/marks) (b) Kenalpastikan semua gula penurun daripada molekul-molekul yang diberi. Bincangkan pilihan anda. Identify all reducing sugars from the molecules given. Discuss your choice(s). (2 markah/marks) (c) Tuliskan mekanisme untuk penukaran bermangkinkan bes bagi D-fruktosa kepada D- glukosa dan D-manosa. Write the mechanism for the base-catalysed conversion of D-fructose into D- glucose and D-mannose. (10 markah/marks) 2/10
3 (d) Sila rujuk kepada skema yang berikut. Please refer to the following scheme. O O O 1. NaB O + W 1. NaB 4 Y 2. 3 O + X O T Br 2, 2 O Tetrose U (i) Berikan struktur bagi W, X dan U Give the structures for W, X and U. (6 markah/marks) (ii) Berikan reagen Y dan keadaan tindak balas (jika ada). Apakah Z? Give the reagent Y and reaction condition (if applicable). What is Z? (2 markah/marks) (iii) Gula V dapat disintesis dari suatu tetrosa. Berikan nama tindak balas tersebut dan kepentingannya. Sugar V can be synthesized from a Tetrose. Provide the name of the reaction and its usefulness. (2 markah/marks) 2. (a) Vitamin C (Asid askorbik) disintesis dari D-glukosa dalam tumbuhan dan hati kebanyakkan vertebrata. Tuliskan skema biosintesisnya. Vitamin C (ascorbic acid) is synthesized from D-glucose in plants and in the livers of most vertebrates. Outline its schematic of biosynthetic pathway. 3/10
4 O O D-glucose O C 2 O O L-ascorbic acid Vitamin C (10 markah/marks) (b) Biodiesel merupakan salah satu aplikasi industri minyak dan lelemak. Lakarkan carta aliran bagi penghasilan biodiesel dari minyak sawit mentah yang mempunyai asid lemak yang rendah. Biodiesel is one of the industrial applications of oils and fats. Sketch the flow chart of the biodiesel production from crude palm oil with low free fatty acids. (5 markah/marks) (c) Olestra adalah penganti lemak yang dipaten oleh Procter dan Gamble yang memimik perisa dan tekstur triasilgliserol. Ia adalah bebas kalori kerana tidak dihidrolisis oleh enzim percernaan dan tidak diserap oleh usus tetapi melalui dalam badan tanpa perubahan. Olestra mengandungi suatu campuran ester asid lemak sukrosa (tidak seperti triasilgliserol yang merupakan ester gliserol asid lemak). Setiap molekul sukrosa dalam olestra diesterifikasi dengan enam hingga lapan asid lemak. Olestra is a fat substitute patented by Procter and Gamble that mimics the taste and texture of triacylglycerols. It is calorie-free because it is neither hydrolysed by digestive enzymes nor absorbed by the intestines but instead is passed directly through the body unchanged. Olestra consists of a mixture of sucrose fatty acid esters (unlike triacylglycerols, which are glycerol esters of fatty acids). Each sucrose molecule in olestra is esterified with six to eight fatty acids. 4/10
5 (i) Lukiskan struktur suatu molekul olestra spesifik yang mengandungi enam asid lemak semulajadi yang telah diesterifikasi pada bahagian tertentu dalam sukrosa. Gunakan tiga asid lemak tepu dan tiga asid lemak tak tepu. Draw the structure of a specific olestra molecule comprising six different naturally occurring fatty acids esterified to any of the available positions on sucrose. Use three saturated fatty acids and three unsaturated fatty acids. (6 markah/marks) (ii) Mengapakah lipasa, yang bertanggungjawab bagi hidrolisis lemak biasa, tidak berupaya menghidroliskan olestra? Why are the lipases, responsible for facilitating normal fat hydrolysis, unable to facilitate the hydrolysis of olestra? (4 markah/marks) 3. (a) Nilai pka untuk lysine (Lys) diberikan di bawah: The pka values for lysine (Lys) are given below: pk 1 = (-CO) = 2.18; pk 2 = (-N 3 + ) = 8.95; pk R (rantai sisi/side chain) = (i) Kira takat isoelektrik (pi) untuk lysine Calculate the isoelectric point (pi) of lysine (2 markah/marks) (ii) Lukiskan struktur lysine apabila ia terlarut di dalam larutan akues yang mempunyai keadaan seperti di bawah: Draw the structure of lysine when it is solvated under an aqueous solution in each of the following conditions: p = 1 p = pi p = 13 (3 markah/marks) 5/10
6 (b) Lukiskan struktur tripeptida is-met-tyr dan berapa ikatan peptida yang terbentuk dan bulatkan? Labelkan N-terminal dan C-terminal. Tandakan dengan * ikatan yang boleh berputar secara bebas and apakah kepentingan ikatan ini? Draw the tripeptide is-met-tyr and how many peptides bonds are present and circle it? Label its N-terminal and C-terminal amino acid. Mark the bond that can rotate freely with * and why is it important? (7 markah/marks) (c) Satu peptida telah dianalisis secara berturutan. A peptide has been analysed sequentially. (i) (ii) idrolisis sepenuh peptida tersebut dengan 6M Cl memberikan is, Pro, Trp, Asp, Cys, Lys dan Glu. Complete hydrolysis of the peptide with 6M Cl gave is, Pro, Trp, Asp, Cys, Lys and Glu. Degradasi Edman untuk peptida tersebut memberikan terbitan PT untuk Cys. Edman degradation of the peptide gave the PT derivative of Cys. (iii) Tindak balas peptida tersebut dengan karboksipeptidasa membebaskan Glu. Reaction of the peptide with carboxypeptidase release Glu. (iv) (v) (vi) Pembelahan peptida tersebut dengan kimotripsin memberikan satu tripeptida (serpihan A) dan satu tetrapeptida (serpihan B). Clevage of the peptide with chymotrypsin gave a tripeptide (Fragment A) and a tetrapeptide (Fragment B). idrolisis Cl bagi serpihan A memberikan Trp, is dan Cys. Cl hydrolysis of Fragment A gave Trp, is and Cys. Degradasi Edman untuk serpihan B memberikan terbitan PT untuk Asp dan satu tripeptida (serpihan C). Edman degradation of fragment B gave the PT derivative of Asp and a tripeptide (Fragment C). 6/10
7 (vii) Degradasi Edman selanjutnya ke atas serpihan C membebaskan Lys dan tiada belahan apabila serpihan C bertindakbalas dengan trypsin. Further Edman degradation on Fragment C release Lys and there is no cleavage when we react Fragment C with trypsin. Dengan menggunakan segala maklumat daripada langkah i vii, tentukan turutan asid amino untuk peptida tersebut. Use all the information from i vii to determine the amino acid sequence for the peptide. (7 markah/marks) (d) Cadangkan sintesis dipeptide Ala-Tyr dengan menggunakan kaedah fasa pepejal Merrifield. Outline a synthesis of dipeptide Ala-Tyr via the Merrifield solid-phase method. (8 markah/marks) 4. Diberikan di bawah adalah blok pembina asid nukleik. Given below are the structures of nucleic acid building blocks. (a) Lukiskan struktur bagi dinucleotide GG di dalam RNA. Draw the structure for the dinucleotide GG in RNA. (7 markah/marks) 7/10
8 (b) Jelaskan perbezaan di antara struktur DNA dan RNA dan berikan penjelasan berdasarkan peranan biokimia mereka. Describe the structural differences between DNA and RNA and explain them based on their biochemical role. (8 markah/marks) (c) Apakah heksapeptida dikodkan oleh serpihan berikut daripada mrna? What hexapeptide is coded for by the following fragment of mrna? 5 - AAA- GUU-GGC-UAC-CCC-GGA-3 (2 markah/marks) (d) Pesawat M17 terhempas di Ukraine. Kesemua 283 penumpang dan 15 anak kapal pesawat telah terkorban. Proses pengecaman identiti ke atas semua mayat yang terkorban boleh dilakukan menggunakan pengecaman DNA. uraikan bagaimana siasatan tersebut boleh dilakukan? Flight M17 crashed in Ukraine. All 283 passengers and 15 crew were killed. The process of identification of all the bodies of the dead can be performed using DNA fingerprinting. Describe how the investigation can be carried out? (6 markah/marks) 8/10
9 Lampiran Attachment Kod genetik The genetic code 9/10
10 20 amino biasa dalam bentuk dominan pada p fisiologi (~7.3) The 20 common amino acids in the form that predominates at physiological p (~7.3) SID2004 Gylcine Alanine Valine Leucine Isoleucine Serine Threonine Cysteine Methionine Phenylalanine Tyrosine Proline istidine Tryptophan Aspartate Glutamate Asparagine Glutamine Lysine Arginine TAMAT END 10/10
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