(a) Draw a structural formula for the products formed when alanine is treated with the following reagents. (20) (0) Fmoc
Posted: Tue May 17, 2022 8:57 am
(a)-(c)
(a) Draw a structural formula for the products formed when alanine is treated with the following reagents. (20) (0) FmocCl, Na2CO3 (ii) BOH, P-TSOH (iii) (Boc)20, NaOH 4 (b) Rink amide resin is an excellent acid-labile support and often used in SPPS to prepare peptide amides. The following synthesis was conducted on the Rink amide resin. Write the structure of the final product A and discuss the cleavage mechanism of the peptide from the resin. (20) NH2 Meo Rink amide resin O Me 1. Fmoc-Val-OH, PYBOP, DMF 2. 20% piperidine in DMF 3. Fmoc-Phe-OH, PyBOP, DMF 4. 20% piperidine in DMF 5. Fmoc-Cys(Tr)-OH, PYBOP, DMF 6. 20% piperidine in DMF 7. Fmoc-Ala-OH, PYBOP, DMF 8. 20% piperidine in DMF 9. TFA/TES/H,O (90:5:5) (TFA = trifluoroacetic acid; TES = triethylsilane) А (c) ( The following cyclic structure is that of arabinose. Is this a furanose or pyranose form? Is it an a on Banomer? Is it a D or L sugar? Explain your reasoning. (20) OH HON HO OH
(a) Draw a structural formula for the products formed when alanine is treated with the following reagents. (20) (0) FmocCl, Na2CO3 (ii) BOH, P-TSOH (iii) (Boc)20, NaOH 4 (b) Rink amide resin is an excellent acid-labile support and often used in SPPS to prepare peptide amides. The following synthesis was conducted on the Rink amide resin. Write the structure of the final product A and discuss the cleavage mechanism of the peptide from the resin. (20) NH2 Meo Rink amide resin O Me 1. Fmoc-Val-OH, PYBOP, DMF 2. 20% piperidine in DMF 3. Fmoc-Phe-OH, PyBOP, DMF 4. 20% piperidine in DMF 5. Fmoc-Cys(Tr)-OH, PYBOP, DMF 6. 20% piperidine in DMF 7. Fmoc-Ala-OH, PYBOP, DMF 8. 20% piperidine in DMF 9. TFA/TES/H,O (90:5:5) (TFA = trifluoroacetic acid; TES = triethylsilane) А (c) ( The following cyclic structure is that of arabinose. Is this a furanose or pyranose form? Is it an a on Banomer? Is it a D or L sugar? Explain your reasoning. (20) OH HON HO OH