Question
Every arm of the 200-megadalton molecule PG5 is terminated by one of these functional groups but protected by a Boc (“bock”). For 10 points each:
[10e] Name this functional group that is protected by Boc or Fmoc (“F-mock”) during peptide synthesis, since it is at the N-terminus of every protein.
ANSWER: amine [or amino group; or NH2 group]
[10m] Synthetic chemists prefer Boc to Fmoc because its deprotection has a higher value for this green chemistry metric. It equals the molecular weight of the desired product divided by the total molecular weight of the reactants.
ANSWER: atom economy [or atom efficiency; or atom percentage; prompt on efficiency; prompt on economy or percentage; reject “yield”]
[10h] Boc-protected peptides are cleaved off the surface using an acidic cocktail containing TIPS, which reacts as one of these nucleophiles to suck up reactive trityl (“TRY-till”) cations. In general, these species react stoichiometrically with inhibitors to prevent side reactions.
ANSWER: molecular scavengers
<Chemistry>
Summary
| 2023 ACF Nationals | 04/22/2023 | Y | 21 | 12.86 | 76% | 38% | 14% |
Data
| Johns Hopkins A | Iowa State A | 10 | 0 | 10 | 20 |
| Maryland A | Chicago A | 0 | 0 | 0 | 0 |
| Claremont A | Cornell B | 0 | 0 | 0 | 0 |
| Indiana A | South Carolina A | 10 | 0 | 0 | 10 |
| WUSTL B | McGill A | 10 | 10 | 0 | 20 |
| Rutgers A | Penn A | 10 | 0 | 10 | 20 |
| UC Berkeley A | Virginia A | 10 | 10 | 0 | 20 |
| Ohio State A | UC Berkeley B | 0 | 0 | 0 | 0 |
| Minnesota A | Vanderbilt A | 10 | 10 | 0 | 20 |
| Brown A | NYU A | 10 | 10 | 0 | 20 |
| Penn State A | Duke A | 0 | 0 | 0 | 0 |
| Florida B | Illinois A | 10 | 10 | 0 | 20 |
| Georgia Tech A | Michigan A | 10 | 0 | 0 | 10 |
| Texas A | Columbia A | 10 | 0 | 0 | 10 |
| Rutgers B | Yale A | 10 | 0 | 0 | 10 |
| Florida A | WUSTL A | 10 | 0 | 0 | 10 |
| Northwestern A | Georgia Tech B | 10 | 10 | 10 | 30 |
| Stanford A | Minnesota B | 10 | 10 | 0 | 20 |
| Toronto A | Yale B | 10 | 0 | 0 | 10 |
| Imperial A | Chicago B | 0 | 0 | 0 | 0 |
| North Carolina A | Cornell A | 10 | 10 | 0 | 20 |