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2. Selective synthesis of the tetrapeptide Ala-Val-Gly-Leu a. Work backward from Structure K to fill in the boxes in the multistep synthesis scheme below. Assume the desired product is purified after each reaction step. Boxes A, B, E, and H should each have a single amino acid with a protecting group. b. Provide names for each indicated structure, using 3-letter codes. The names do not have to take protonation state into account but should account for protecting groups. B R A F ; name: G Boc- a Boc-amino acid name: K H₂N. HOL OF₂ CF3 НО name: Start here and work backward -OEt an amino acid ethyl ester Ala-Val-Gly-Leu E ¡H R N=C=N N=C=N (EtOH) R R PN=C=N R NaOH (excess) R C name: D ! name: name: J name: | HOCF₂ НО 요 HO CF3 c. Suppose that you wanted to synthesize Ala-Lys-Glu using this same multistep synthesis method. What problem would occur? Propose a conceptual idea (not specific reactions) of how the problem could be solved. (Hint: look up the functional groups present in these amino acid structures)

2. Selective synthesis of the tetrapeptide Ala-Val-Gly-Leu a. Work backward from Structure K to fill in the boxes in the multistep synthesis scheme below. Assume the desired product is purified after each reaction step. Boxes A, B, E, and H should each have a single amino acid with a protecting group. b. Provide names for each indicated structure, using 3-letter codes. The names do not have to take protonation state into account but should account for protecting groups. B R A F ; name: G Boc- a Boc-amino acid name: K H₂N. HOL OF₂ CF3 НО name: Start here and work backward -OEt an amino acid ethyl ester Ala-Val-Gly-Leu E ¡H R N=C=N N=C=N (EtOH) R R PN=C=N R NaOH (excess) R C name: D ! name: name: J name: | HOCF₂ НО 요 HO CF3 c. Suppose that you wanted to synthesize Ala-Lys-Glu using this same multistep synthesis method. What problem would occur? Propose a conceptual idea (not specific reactions) of how the problem could be solved. (Hint: look up the functional groups present in these amino acid structures)

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
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2. Selective synthesis of the tetrapeptide Ala-Val-Gly-Leu a. Work backward from Structure K to fill in the boxes in the multistep synthesis scheme below. Assume the desired product is purified after each reaction step. Boxes A, B, E, and H should each have a single amino acid with a protecting group. b. Provide names for each indicated structure, using 3-letter codes. The names do not have to take protonation state into account but should account for protecting groups. B R F name: G Boc- a Boc-amino acid name: K H₂N. OH name: 요 CF3 Start here and work backward -OEt an amino acid ethyl ester Ala-Val-Gly-Leu E H R R N=C=N N=C=N (EtOH) N=C=N R R NaOH (excess) R C name: D name: name: J name: над око CF 3 HO 요 CF3 c. Suppose that you wanted to synthesize Ala-Lys-Glu using this same multistep synthesis method. What problem would occur? Propose a conceptual idea (not specific reactions) of how the problem could be solved. (Hint: look up the functional groups present in these amino acid structures)
Transcribed Image Text:2. Selective synthesis of the tetrapeptide Ala-Val-Gly-Leu a. Work backward from Structure K to fill in the boxes in the multistep synthesis scheme below. Assume the desired product is purified after each reaction step. Boxes A, B, E, and H should each have a single amino acid with a protecting group. b. Provide names for each indicated structure, using 3-letter codes. The names do not have to take protonation state into account but should account for protecting groups. B R F name: G Boc- a Boc-amino acid name: K H₂N. OH name: 요 CF3 Start here and work backward -OEt an amino acid ethyl ester Ala-Val-Gly-Leu E H R R N=C=N N=C=N (EtOH) N=C=N R R NaOH (excess) R C name: D name: name: J name: над око CF 3 HO 요 CF3 c. Suppose that you wanted to synthesize Ala-Lys-Glu using this same multistep synthesis method. What problem would occur? Propose a conceptual idea (not specific reactions) of how the problem could be solved. (Hint: look up the functional groups present in these amino acid structures)
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