{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

FINAL - Student Name Problem 3 Determine the amino acid...

Info icon This preview shows pages 1–15. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 8
Image of page 9

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 10
Image of page 11

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 12
Image of page 13

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 14
Image of page 15
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Student Name: Problem 3 Determine the amino acid sequence of a polypeptide from the following results: (Explain briefly your reasoning). 1. Complete hydrolysis of the peptide yields the following amino acids: Ala, Arg, Gly, 2 lys, Met, Phe, Pro, 2 Ser, Tyr, Val. ' ‘ ‘ Treatmentwith Edman’s reagent releases Val Carboxypeptidase A releases Ala. Treatment with cyanogen bromide yields the following two peptides: a) Ala, 2.Lys, Phe, Pro, Ser, Tyr ' b) Arg, Gly, Met, Ser, Val 5. Treatment with chymotrypsin yields. the following three peptides: a) 2 Lys, Phe, Pro ’ b) Arg, Gly, Met, Ser, Tyr, Val c) Ala, Ser 6. Treatment with trypsin yields the following three peptides: a) Gly, Lys, Met, Tyr b) Ala, Lys, Phe, Pro, Ser c) Arg, Ser, Val. 5‘9"!" Reminder: The endopeptidases trypsin and chymotrypsin will not catalyse the hydrolysis of an amide band if proline is at the hydrolysis site.. Amino acid—Praline No hydrolysis on the C-side of the amino acid éKPlanarl'xe-A ' ‘ . . WA Nvl-ermtnal ammfi ““43 ' .- k Edmar‘ C -\-€rr«\§rwtl lem “03$ 3 A“ ® ‘Akg .__.._g 4‘ CMEGBP‘LP‘k‘): (mmng ma}- ML? (1“ [33%ka ‘5 x. CNEM" < p. *1 Qljgol'fjpsia 1 ( TQ: $610 a)? x. Tt‘bfs’o (%§\_\23 5 (lard? wamggflffl’rgé95fioflkflk Hrs 11%t2222~|%1( O Student Name: After treating the following tetrapeptide with 2,4—dinitrofluoro benzene (2,4-DNFB) followed by 7 complete hydrolysis, we isolate two different 2,4-dinitrophenyl—derivatized amino acids. Phe-Ser-Lys-Val a) Draw the three dimensional structures, including the 2,4-dinitrophenyl group if present, for each of the four amino acids obtained. ' b) Draw the chemical structure of the major products expected from each of the following reactions (with respect to the stereochemistry). ©N=C=S ' HF Phe-Ser Problem 8 Provide the major products for each of the following reactions. CH3 CH3 ) Mg/Ether NQH a - Br <2)ij H+/H20 ‘ B H , D) W .______3__> WON Hzoz/NaOH 6) H20 .. o) W _..___.—» <3) ‘ H2504 A3): 6r B NH d) /\n/H _.:2___. A: /H’/H V \ 0 H+(H20) @ O 1) (CH2=CHCH2)QCuLi e) _________________, k 2) H+/H20 C5) 0 f) o LDA, THF, -60°C 64 v / CV” C3) Student Name: 11 Student Name: Prghlem 6 What are the compounds obtained in each case following treatment of the tripeptide Ala-Lys-Phe under the given conditions (:pay attention to the stereochemistry). a) GM (HCI), 200°C 1) _ OzNQF b) N02 2) EN (HCI), 200°C ® ,9 1)©—N=C=S S d), >MNN\ 2)HéF‘ Iv ‘ (5/ \ID // ' Student Name: x" Problem 2 ' ‘ ' a) Starting from polystyrene methyl chloride 0“ resin: ’ Using the appropriate reagents and techniques, provide a synthetic approach for the solid-phase synthesis of the tetrapeptide: . Phe-Ser-Lys-Val m 1.x ......... (M @a ‘ I I. -.. 3....“ x- f ‘ ‘ . - ' A ‘ 2; _ .- ’ .- 1) ") Omar Whitest». @ ) fires (can) am a )5?an b) Draw the chemical structure of the major products expected from each of the following reactions (with respect to the stereochemistry). , HF Lysv-Vél Student Name: Problem 2 a) Starting from polystyrene methyl chloride Cl/\. resin: Using the appropriate reagents and techniques, provide a synthetic approach for the solid-phase synthesis of the tetrapeptide: A Phe-Ser-Lys-Val o ,hfi 0 1,5,0 w:\fiux‘° £001: r “wt? b) Draw the chemical structure of the major products expected from each of the following reactions (with respect to the stereochemistry). ©—N=C=S . . . HF ., Lys-Val Student Name: Emu—0111.2. Using Strecker synthesis and appropriate reagents and techniques, provide a synthetic approach for the synthesis of L-Leucine from isobutyl chloride. ' . ‘ Now I \/\ I» ‘4qu \\ H dL. ———9 CM .. /° r' / 1’ ' . Student Name: I 1 Problem 1 21) Using Strecker synthesis and appropriate reagents and techniques, provide a synthetic approach ‘ for the synthesis of Boc-Lys(§-Fmoc)—OH from 3-Chloro-propylamine. b) Starting from Boc-Lys(§-Fmoc)-OH, proline, and valine methyl ester, provide a strategy for the synthesis in solution of the tripeptide: Lys-Pro-Val. Show the chemicalistructures of all intermediates and provide all the reagents needed for all steps to ‘ perform the synthesis. ° ' ' ' 0:) Hz Name: Student ID: ****************§l¢*********************************************** ********************* n A , ' + a f“ ‘ A) Provide all the reagents needed for the following transformation. CZ) Show all the intermediates and provide the meehanisms involved. 0 .0 0“ gum/mo (j ————+& F——- J54) Name: - H Student ID: ****************alt***‘***********’l¢*********************$*’********* ********************* A) Provide all thereagentéflneeded fer the followingtranéfonnation. ( a @ .' Show all the intermediates and provide the mechanisms involved. * , ° . ‘ ° '02” AONQOH/Htofij _________‘ ii "_______ *4) {>8}le " v l . M ng ' flea! - " I Provide thg detailed mechanism for the steps: C ‘-->_D e» E; Student Name: Problem 2 , What are the expected products for the following reactions. Propose reasonable mechanisms for both reactions Pay attention to the stereochemistry and name the final products a) + o ”‘03 ”Gun”; H+ ' K )H2 //"oj\'/ <* H «M W HCI, ethanol L 14— “” H N 0—- / Qa’ (M 14 4-,! '4 \ 113.... / 5 5 2 O, “\ f W a / um“: \% o\ M \ NH “LN fig Cub 2:341“ {€4.21 1mg Us ”Lt" \ /Ufg w, I Student Name: Problem 5 a) Write structural formulas for all compounds indicated by letters. Pay attention to the stereochemistry. CH3O-SOZ-OCH3 H30”, heat TsCI, pyndme a-D—Gluoose W A B —-——————> NaOH, H20 SNaOH H20 014 0 ‘ 0W3 , we Student Name: s Prgblem 4 Give the product(s) that are Obtained when D-galactose reacts with the following: CHO ' - H OH i ) Coon HO H ' ’ ‘ o. E H HO H . H o H > H OH H 0 ‘ H , ' CH20H , Ho H a H a“ D-galactose , . ‘ QboW a) nitric acid b) Br 2, H20 H c) H2/Pd/C C) 041° A) d) 3 eq of phenyl hydrazine k a VI e) ethanol/HCI HO H f) 1) Br2/H20; 2) H202, Fe3+ @ Ho t4 ( L) h) CH3l, A920 H ow (Lu 2. O M Q . o > k: \ ‘0sz5 +H A“/ \A‘/" No W Ho 0% AB ”C“ (M 429w”) 9) h), 9 CH H OH 3 equivalents of HO H --—-——-- H a H OH Ph-NH-NHg H OH \CHZOH c“) I CH H OH Ethanol v Ho H " H OH HCI H OH CHgOH 9 CH H OH 1) Bra in water HO H ___________. H OH 2) Ca(OH)2, Fe3"', H20 H OH ' CH20H NaOH/HQO ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern