Sohora, Margareta; Šumanovac Ramljak, Tatjana; Mlinarić-Majerski, Kata; Basarić, Nikola
Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives.
Croatica chemica acta, 87
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 dipeptide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated electron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation products, whereas N-adamantyl derivatives also give cyclization products.
||Photodecarboxylation, Dipeptides, Phthalimides
||NATURAL SCIENCES > Chemistry
||Division of Organic Chemistry and Biochemistry
|Project title||Project leader||Project code||Project type|
|Fotokemija policikličkih molekula: od istraživanja mehanizama reakcije do novih lijekova i medicinskih primjena|| Basarić Nikola||UIP-02.05/25||HRZZ|
|Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima|| Kata Majerski||098-0982933-2911||MZOS|
||10 Mar 2015 14:26
||05 May 2015 13:32
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