(a) Draw a structural formula for the products formed when alanine is treated with the following reagents. (i) (Boc)20, NaOH (ii) CbzCI, NazCO3 (iii) 2-Methylpropene, p-TSOH

Chemistry: Principles and Reactions
8th Edition
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:William L. Masterton, Cecile N. Hurley
Chapter23: Organic Polymers, Natural And Synthetic
Section: Chapter Questions
Problem 31QAP: On complete hydrolysis, a polypeptide gives two alanine, one leucine, one methionine, one...
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(a) Draw a structural formula for the products formed when alanine is treated with the following
reagents.
(i) (Boc)20, NaOH
(ii) CbzCI, NazCO3
(iii) 2-Methylpropene, p-TSOH
(b) Enfuvirtide, a 36-amino-acid peptide drug, was manufactured at a multi-tonne per year scale. The
manufacture relied on solid phase synthesis with Barlos resin as the solid support. Part of the solid
phase synthesis is shown below. Write the structure of the product A and discuss the cleavage
mechaniśm of the peptide from the resin.
1. Fmoc-Leu-OH, DIPEA
2. 20% piperidine in DMF
3. Fmoc-Glu('Bu)-OH, HBTU, HOBt
4. 20% piperidine in DMF
5. Fmoc-Leu-OH, HBTU, HOBT
6. 20% piperidine in DMF
7. Fmoc-Leu-OH, HBTU, HOBE
8. 20% piperidine in DMF
9. 10% HOAC in CH2CI2
Barlos resin
Transcribed Image Text:(a) Draw a structural formula for the products formed when alanine is treated with the following reagents. (i) (Boc)20, NaOH (ii) CbzCI, NazCO3 (iii) 2-Methylpropene, p-TSOH (b) Enfuvirtide, a 36-amino-acid peptide drug, was manufactured at a multi-tonne per year scale. The manufacture relied on solid phase synthesis with Barlos resin as the solid support. Part of the solid phase synthesis is shown below. Write the structure of the product A and discuss the cleavage mechaniśm of the peptide from the resin. 1. Fmoc-Leu-OH, DIPEA 2. 20% piperidine in DMF 3. Fmoc-Glu('Bu)-OH, HBTU, HOBt 4. 20% piperidine in DMF 5. Fmoc-Leu-OH, HBTU, HOBT 6. 20% piperidine in DMF 7. Fmoc-Leu-OH, HBTU, HOBE 8. 20% piperidine in DMF 9. 10% HOAC in CH2CI2 Barlos resin
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