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Week 12 Worksheet Answers

Week 12 Worksheet Answers - Organic Chemistry it Week 12...

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Unformatted text preview: Organic Chemistry it Week 12 worksheet Not for credit Draw the structure of each amino acid below. Show the correct stereochemistry and the correct protonation and charges for the amino acid at pH 7.0- L-Glutamine L—Aspartic Acid L—Arginine D—Cysteine O l . N H - Q ““2. . 2“ .7 o _ JL .. /\\‘- 0‘5 /fit NHL ti“ “/0 /L(oO—- f5” ‘" (I) N (-3 5 G) is o "a was Which amino acid has the most acidic side chain? . Aspar-Hc x4r—t‘c/ Which amino acid has the most basic side chain? Ara rm f n 6. Which two amino acids (one basic and one acidic) have side chain pKa’s near pH 7, making them useful for shuttling protons in acid—base catalysis, under physiological conditions? Basic: "JP 24:“: fr‘a/I'n e_ 4c rip/Kc. ”b Cir/Skin Q Identify 2 (of 5 possible) amino acid side chains that can act as nucleophiles, in reactions we are already familiar with. or! our #044 +5)st g” "fro” 1’ SH i 0 ‘5'” do): ' -t- H [U ”I: H I - "' gar-Cake ~Hnreonin-2- .Hi;+ . 34,9 CL?)- H3M CD7— , c. sic—Pne— l‘oSt Ag. What is the isoelectric point of alanine? Draw the structure(s) of alanine that exist at its isoelectric point. PI”:- é.// HN 0‘9 3 69 What are the isoelectric points of glutamic acid and lysine. Draw the structures(s) of each at their isoelectric point. ’* -.-—“- _ I 9' ch74 @143 ? J” 3 03‘ O O H 5t) i ”35 ($02?” ’32” 0019 Draw the structure of the dipeptide ValTyr at pH 7. Draw the two forms of this structure, with the peptide bond in the s-cis and s—trans conformations. Which of these conformations is preferred? Sfrfmns pref-c rrccf S-CI‘S tof2 O Draw the products when the following peptide is treated with cyanogen bromide. For each product, use the letter abbreviations for the amino acids that are unaffected by the reaction. Show the structures of the products at the end of the peptides. C5 C9 @NH~G45Hr'sTerailqlcu—-LE 00 GIyHisTyayaIAiaMegbluAsnLeuIIeMe rp 3 U ° # @lgN—GluA‘SnLCab—‘Elefim G) H N ~17. ”Cog-3 \f 3 P What would the products be if the above peptide were cleaved with chymotrypsin? .4} 613 H‘CsTflr ‘3 Val/41a Mc+ aft/ism [fig .27.; AM 73, What would the products be if the above peptide were subjected to Edman degradation? 63%} ~— tics'rjj rVal fHa Mc‘l' eh... Hm gets 17: M 730 HA) —\,.. 5%“ro \.. Describes the differences between arfihhelix and a B—pleated sheet. Specifically, how are the amide bonds are oriented differently between the two structures? How are the side chains oriented differently? 03*ha/rx-> curve/e éaflc/S araZ/a/ balls 64; Ana/r9; _ ‘ 4. .9 Sl‘dc GJ/Iatlng Pfrpwdr‘cujar 76 My; c376 \éZ/V 5’Shéc’n" “jaMrK/e 6045 PMPbVICIIC—ooéar gé: an: cg 5/73514— _ ‘3‘3/‘9- Chains a/krncsréfl aécpue: quad be Aim) “14519 S/(eg‘H What force holds these structures together? is it intermolecular or intramolecular? #3 c/roje/A bong/5 '— . £44m MO/CCCL/d. r 44“” q/—- ”506 2. Zn 'fTOMO/fch/Qr" (CIDCCc'cs/dnazg /}I7£crk/VLO Edie/aw] {gr- 5,—34681 A decapeptide has the following amino acid composition: Ala(2), Arg, Met, Glu, Giy, Leu, Lys, Phe, Val Partial hydrolysis provides the following tripeptidee; Met—Glu-Leu + Gly-Arg—Met + Leu-Ala—Ala + Lys—Val-Phe + Val—Phe-Gly One round of Edman degradation yields a‘ lysine phenylthiohydantoin- ‘ Treatment of this peptide with cyanogen bromide results in two peptides. One of these peptides, upon complete hydrolysis, provides the following amino acids: Ala(2), Glu, Leu. From this information, deduce the primary structure of this decapeptide- i 495 Va We 4/7 43. 115+ ear 4m. 41a 4/4. 20f2 ...
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Week 12 Worksheet Answers - Organic Chemistry it Week 12...

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