Croatica Chemica Acta, Vol. 87 No. 4, 2014.
Original scientific paper
https://doi.org/10.5562/cca2482
Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives
Margareta Sohora
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Tatjana Šumanovac Ramljak
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Kata Mlinarić-Majerski
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Nikola Basarić
orcid.org/0000-0001-9412-9734
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Abstract
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.
Keywords
photodecarboxylation; dipeptides; phthalimides
Hrčak ID:
131545
URI
Publication date:
22.12.2014.
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