Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives
| Autor: | Nikola Basarić, Tatjana Šumanovac Ramljak, Margareta Sohora, Kata Mlinarić-Majerski |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Dipeptide
010405 organic chemistry Decarboxylation Electron donor General Chemistry photodecarboxylation dipeptides phthalimides 010402 general chemistry Photochemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Phthalimide Chemistry chemistry.chemical_compound chemistry Flash photolysis Moiety Carboxylate Selectivity |
| Zdroj: | Croatica Chemica Acta Volume 87 Issue 4 Croatica chemica acta |
| ISSN: | 1334-417X 0011-1643 |
| Popis: | New dipeptide derivatives 1 and 3 were synthesized and their reactivity in the photochemical reaction of decarboxylation was investigated. The photodecarboxylation of N-adamantyl derivatives 1a and 1b and N-phenylphthalimide derivatives 3a and 3b probably takes place from the triplet excited state. The triplet excited state of 1a, 3a and 3b was characterized by laser flash photolysis. N-phenylphthalimides 3a and 3b undergo 2−5 times more efficient photodecarboxylation than N-adamantylphthalimides 1a and 1b. The aminoacid residue (Phe or Gly) at the C-terminus of the dipep-tide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated elec-tron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation prod-ucts, whereas N-adamantyl derivatives also give cyclization products. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|