(Kertas soalan ini mengandungi 8 soalan dalam 10 halaman yang dicetak) (This question paper consists of 8 questions on 10 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 PEPERIKSAAN IJAZAH SARJANA MUDA SAINS DENGAN PENDIDIKAN EXAMINATIN FR THE DEGREE F BACHELR F SCIENCE WITH EDUCATIN SESI AKADEMIK 2014/2015 : SEMESTER 1 ACADEMIC SESSIN 2014/2015 : SEMESTER 1 SCES2262 : KIMIA BIMLEKUL BIMLECULE CHEMISTRY Disember 2014/Januari 2015 December 2014/January 2015 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALN : INSTRUCTINS T CANDIDATES : Jawab SEMUA soalan. Answer ALL questions. (Kertas soalan ini mengandungi 8 soalan dalam 10 halaman yang dicetak) (This question paper consists of 8 questions on 10 printed pages)
2 1. Pertimbangkan formula struktur berikut. Examine the following structural formulas. H 2 C H (a1) (a2) H H 2 N H (A) n H (b1) H H H (B) (b2) H H H H H H (c3) (c1) H H H H H H H (C) (c2) H H H H H H H H 2 N H C 2 H H CH 3 (D) (E) (F) (G) (a) Kelaskan semua monosakarida dan oligosakarida di atas kepada gula penurun dan gula bukan penurun. Classify all mono- and oligosaccharides above into reducing and non-reducing sugars. Kelaskan semua unit ketosa di atas mengikut saiz gula. Classify all ketose building blocks above according to sugar size. (10 markah/ marks) 2. Satu monosakarida ditakrifkan sebagai L-3-amino-3,7-dideoxy-aldoheptosa dengan konfigurasi stereokimia ABABB. A monosaccharide is defined as L-3-amino-3,7-dideoxy-aldoheptose with relative stereochemistry ABABB. (a) (c) Lukis unjuran Fischer bagi monosakarida tersebut. Draw the Fischer projection of the monosaccharide. Lukis struktur 3D bagi pusat stereokimia di C-4 dan tandakan konfigurasi mutlak. Draw a 3D-structure for the stereocentre at C4 and assign the absolute configuration. Bina unjuran Haworth bagi -furanosa. Construct the Haworth projection of the -furanose. (13 markah/ marks) 2/10
3 3. Pertimbangkan glicosida berikut. Examine the following glycosides. CH 3 H H H H H H CH 3 H-a H-b (a) Berikan mechanisme bagi sintesis Fischer sintesis untuk glikosida H dan jelaskan stereokimia untuk hasil tindak balas. Provide the reaction mechanism for the Fischer-glycosylation of glycoside H and explain the stereochemical output of the reaction. Jelaskan mengapa sintesis glikosida H-β adalah sangat sukar. Explain why the synthesis of glycoside H- is very difficult. (8 markah/ marks) 4. Tunjukkan bagaimana aldosa dan ketosa boleh ditukar antara satu sama lain dalam teadaan bes, menggunakan triosa aldehid gliserat dan dihidroksi-aseton sebagai contoh. Show how aldoses and ketoses can be interconverted to each other under basic conditions, using the trioses glyceric aldehyde and dihydroxy-acetone as example. (4 markah/ marks) 5. Tidak seperti DNA yang mengelkalkan kod maklumat genetik spesies, RNA biasanya diperlukan hanya sementara semasa biosintesis protein. Unlike DNA, which permanently codes the genetic information of species, RNA is usually needed only temporarily during the protein biosynthesis. (a) Bagaimana struktur RNA berbeza daripada DNA? How does the structure of RNA differ from DNA? Tulis mekanisme untuk kitar semula nukleotida daripada RNA, dengan menggunakan model ringkas dinukleosida (bes boleh disingkat kan sebagai R). Write the mechanism for the recycling of nucleotides from RNA, using a simplified dinucleotide model (bases can be abbreviated as R). 3/10
4 (c) Namakan dan huraikan semua peringkat untuk biosintesis protein. Jelaskan bagaimana langkah tersebut berfungsi dan mengapa mereka diperlukan. Name and describe all stages for the protein biosynthesis. Explain how the steps work and why they are required. (15 markah/ marks) 6. (a) Berikan nama sistematik DAN nama ringkasan untuk setiap asid lemak yang ditunjukkan di bawah: Provide the systematic name AND short hand representation for each of the fatty acid below. (5 markah/ marks) Bulatkan unit isoprena untuk terpena berikut dan kelaskan mereka sebagai monoterpena, sesquiterpena, diterpena, dll. Circle the isoprene units in the following terpenes and classify them as monoterpene, sesquiterpene, diterpene, etc. (6 markah/ marks) 4/10
5 (c) Berikan reagen atau hasil untuk SEMUA reagen dan hasil (A H) bagi transformasi-transformasi berikut: Give reagents or products for ALL reagents and products (A H) for the following transformations: (8 markah/ marks) 7. (a) Nilai pk a untuk arginine (Arg) diberikan di bawah: The pk a values for arginine (Arg) are given below: pk 1 ( CH) = = 1.82; pk 2 ( NH 3 + ) = 8.99; pk R (rantai sisi/side chain) = (i) Kira takat isoelektrik (pi) untuk arginine Calculate the isoelectric point (pi) of arginine 5/10
6 (ii) Lukiskan struktur arginine apabila ia terlarut di dalam larutan akueus yang mempunyai keadaan seperti di bawah: Draw the structure of arginine when it is solvated under an aqueous solution in each of the following conditions: ph = 1 ph = 14 ph = pi (5 markah/ marks) Berikan reagen atau hasil untuk SEMUA reagen dan hasil (J N) bagi transformasi-transformasi berikut: Give reagents or products for ALL reagents and products (J N) for the following transformaions: (6 markah/ marks) 6/10
7 8. (a) Jelaskan terma denaturasi protein dan berikan dua contoh keadaan yang akan menyebabkan denaturasi protein. Explain the term denaturing of protein and provide two examples of a condition which causes denaturing of a protein. (6 markah/ marks) Satu peptida telah dianalisis secara berturutan. A peptide has been analyzed sequentially. (i) (ii) Hidrolisis sepenuh peptida tersebut dengan 6 M HCl memberikan His, Trp, Asp, Cys, dan Glu. Complete hydrolysis of the peptide with 6 M HCl gave His, Trp, Asp, Cys, and Glu. Degradasi Edman untuk peptida tersebut memberikan terbitan PTH untuk Cys. Edman degradation of the peptide gave the PTH derivative of Cys. (iii) Tindak balas peptida tersebut dengan karboksipeptidasa memberikan Glu pada mulanya. Reaction of the peptide with carboxypeptidase gave Glu initially. (iv) (v) (vi) Pembelahan peptida tersebut dengan tripsin memberikan satu dipeptida (Serpihan A) dan satu tripeptida (Serpihan B). Cleavage of the peptide with trypsin gave a dipeptide (Fragment A) and a tripeptide (Fragment B). Hidrolisis HCl bagi Serpihan A memberikan Trp dan Cys. HCl hydrolysis of Fragment A gave Trp and Cys. Degradasi Edman untuk Serpihan B memberikan terbitan PTH untuk His dan satu dipeptida (Serpihan C). Edman degradation of Fragment B gave the PTH derivative of His and a dipeptide (Fragment C). Dengan menggunakan segala maklumat daripada langkah i vi, tentukan turutan asid amino untuk peptida tersebut. Use all the information from i vi to determine the amino acid sequence for the peptide. (6 markah/ marks) 7/10
8 (c) Cadangkan sintesis tripeptida yang berikut dengan menggunakan kaedah fasa pepejal. Nyatakan kebaikan-kebaikan sintesis kaedah fasa pepejal. utline a synthesis for the following tripeptide via the solid-phase method. State the advantages of solid phase peptide synthesis. (8 markah/ marks) 8/10
9 Lampiran 1 Attachment 1 20 asid amino biasa dalam protein The 20 common amino acids in proteins 9/10
10 Lampiran 2 Attachment 2 Penggandaan berangka IUPAC IUPAC numerical multiplier Number Multiplier 1 mono- 2 di- 3 tri- 4 tetra- 5 penta- 6 hexa- 7 hepta- 8 octa- 9 nona- 10 deca- 11 undeca- 12 dodeca- 13 trideca- 14 tetradeca- 15 pentadeca- 16 hexadeca- 17 heptadeca- 18 octadeca- 19 nonadeca- 20 icosa- 21 henicosa- 22 docosa- 23 tricosa- 30 triconta- 31 hentriconta- TAMAT END 10/10
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